title string | abstract string | doi string | has_route int64 |
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Simple and Efficient Solution-Phase Synthesis of Oligonucleotides Using Extractive Work-Up | A solution-phase synthesis protocol amenable to scale-up was developed for the preparation of oligonucleotides employing phosphoramidite chemistry and DMTr/iBu/Bz-protected monomers. Isolation of intermediates was accomplished by means of extractions as the only purification tool. The potential of the method is demonst... | 10.1021/op060133q | 0 |
Practical Synthesis of a Heterocyclic Immunosuppressive Vitamin D Analogue | 1α,25-Dihydroxyvitamin D 3 (calcitriol) 1 and synthetic analogues thereof are highly potent compounds with a wide range of pharmacological activity making them of great interest for the pharmaceutical industry. Herein we report an improved synthesis of the calcitriol analogue 2, which features a novel oxazole-containin... | 10.1021/op060130d | 1 |
Research and Development of an Efficient Process for the Construction of the 2,4,5-Substituted Pyridines of NK-1 Receptor Antagonists | Roche has identified a 2,4,5-trisubstituted pyridine template for a new class of potent NK 1 receptor antagonists. Previous strategies for construction of the pyridine core of these NK-1 receptor antagonists involved functionalization of a 2,5-disubstituted pyridine. We now report on construction of the pyridine core f... | 10.1021/op060128m | 1 |
Synthesis of (<i>S</i>)-3-(<i>N</i>-Methylamino)-1-(2-thienyl)propan-1-ol: Revisiting Eli Lilly's Resolution−Racemization−Recycle Synthesis of Duloxetine for Its Robust Processes | (±)-3-( N, N -Dimethylamino)-1-(2-thienyl)propan-1-ol ( 6 ), prepared from 2-acetylthiophene ( 4 ) in a two-step overall yield of 79%, is resolved into ( S )- 6 of 93% ee as its diastereomeric salt ( 8 ) with ( S )-mandelic acid ( 7 ) according to Eli Lilly's procedures developed for the resolution−racemization−recycle... | 10.1021/op060118l | 1 |
Process Development toward the Pilot Scale Synthesis of the Piperidine-Based Cocaine Analogue and Potent Dopamine and Norepinephrine Reuptake Inhibitor CTDP 31,446 | (+)-Methyl 4β-(4-chlorophenyl)-1-methylpiperidine-3α-carboxylate hydrochloride (CTDP 31,446) is known as a dopamine reuptake inhibitor. This cocaine analogue lacking the tropane skeleton is being considered for potential treatment of cocaine addiction. Herein we report the development of a scalable process for the prep... | 10.1021/op060114g | 1 |
Lab Automation in Support of Safer Process Design for HWE Reaction | A scaleable process technology has been developed for a Horner−Wadsworth−Emmons reaction. The basic calorimetry capability of the MultiMax automated reactor system afforded some interesting insights regarding scale-up safety of the original process and helped guide us to improve alternative chemistry more suitable for ... | 10.1021/op060110b | 0 |
A Practical and Scaleable Preparation of 1,4-Anhydroerythritol | A practical and efficient kilogram-scale preparation of 1,4-anhydroerythritol from meso -erythritol is described. A novel silica gel and sodium bicarbonate slurry/filtration protocol is utilized to purify the product, giving commercial-grade material in 60−65% yield. | 10.1021/op0601058 | 0 |
Synthesis of 4-Cyano Pyrroles via Mild Knorr Reactions with β-Ketonitriles | Mild methods for conducting Knorr chemistry with β-ketonitriles were developed. This enabled the preparation of 4-cyano-penta-substituted pyrroles and gave access to α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor potentiators for biological evaluation. In addition, a series of alkyl and aryl β-ket... | 10.1021/op060104f | 1 |
Oxidation of 4-Halo-2-nitrotoluene with Tetrabutylammonium Permanganate in Pyridine: Development and Safety Evaluation | 4-Halo-2-nitrobenzoic acids are synthesized by oxidation of 4-halo-2-nitrotoluene with tetrabutylammonium permanganate (TBAP) in pyridine in multigram quantities. A significant induction period is observed at room temperature, and the vigorous exothermic reaction presents the risk of a run-away reaction. By control-fee... | 10.1021/op060102v | 0 |
A Concise, Economical, and Diastereoselective Synthesis of Methyl DGJ Isopropylidene: An Iminocyclitol Molecule Core for Analogue Synthesis | A six-step synthesis of the title compound starting from l -lyxonolactone 2,3-isopropylidene ( 6 ) is described. The synthesis is achieved by conversion of 6 to the C 5 -triflate or C 5 -mesylate 7a or 7b and their displacement by sodium azide to yield the C 5 azido compound 8 . Addition of methylmagnesium bromide and ... | 10.1021/op060100a | 0 |
Development of a Scalable and Safe Procedure for the Production of (3<i>R</i>)-3-(2,3-Dihydro-1-benzofuran-5-yl)-1,2,3,4-tetrahydro-9<i>H</i>-pyrrolo[3,4-<i>b</i>]- quinolin-9-one, an Intermediate in the Synthesis of PDE-V Inhibitors RWJ387273 (R301249) and RWJ444772 (R290629) | A scalable and safe process for the oxidative rearrangement of β-carboline to quinolone derivatives, intermediates in the synthesis of PDE-V inhibitors RWJ387273 (R301249) and RWJ444772 (R290629), has been developed. | 10.1021/op060099f | 1 |
Efficient Synthesis of a Highly Selective NPY-5 Receptor Antagonist: A Drug Candidate for the Treatment of Obesity | A concise and practical synthesis of highly selective NPY-5 receptor antagonist 1 is described. The animopyrazine intermediate 3 was synthesized via either monobromination of aminopyrazine or palladium-catalyzed regioselective debromination of dibromopyrazine followed by an efficient Suzuki−Miyaura coupling. For the pr... | 10.1021/op0600963 | 1 |
A Simple Preparation of a (Pyridonyl-1)propargylacetic Acid Derivative | (Pyridonyl-1)propargyl malonate 7 was prepared through two consecutive alkylations of pyridone 2 with ethyl bromomalonate and propargyl bromide in one pot in nearly quantitative yields. Malonate 7 was hydrolyzed to give racemic acid (±)- 1, which was then resolved with (−)-norephedrine to give ( S )- 1 . The recovered ... | 10.1021/op0600916 | 1 |
Process Development and Scale-Up of PPAR α/γ Dual Agonist Lobeglitazone Sulfate (CKD-501) | A scaleable synthetic route to the potent PPARα/γ dual agonistic agent, lobeglitazone ( 1 ), used for the treatment of type-2 diabetes was developed. The synthetic pathway comprises an effective five-step synthesis. This process involves a consecutive synthesis of the intermediate, pyrimidinyl aminoalcohol ( 6 ), from ... | 10.1021/op060087u | 1 |
Development of a Scalable Synthetic Route towards a Thrombin Inhibitor, LB30057 | Described is a scalable synthetic route towards LB30057 ( 1 ) which is based upon a chiron approach using methyl tyrosinate hydrochloride as a starting material. In situ protection of methyl tyrosinate to its N,O -bis-trimethylsilyl derivative and subsequent N -selective introduction of naphthalenesulfonyl group provid... | 10.1021/op060083p | 1 |
Organic Light-Emitting Devices: Synthesis, Properties and Applications Edited by K. Mullen and U. Scherf. Wiley-VCH: Weinheim. 2006. xvii + 410 pp. £139. ISBN 3-527-31218-8. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTOrganic Light-Emitting Devices: Synthesis, Properties and Applications Edited by K. Mullen and U. Scherf. Wiley-VCH: Weinheim. 2006. xvii + 410 pp. £139. ISBN 3-527-31218-8.Cite this: Org. Process Res. Dev. 2006, 10, 5, 1081Publication Date (Web):May 24, 2006Publication H... | 10.1021/op060080c | 0 |
Development of a Synthetic Process towards a Hepatitis C Polymerase Inhibitor | The synthesis of 2-(4-{2-[(2 R )-2-Cyclopentyl-5-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-4-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl]-ethyl}-2-fluoro-phenyl)-2-methyl-propionitrile ( 1 ) on multikilogram scale is described. Initial synthesis of this clinical candidate for inhibition of the hepatitis C v... | 10.1021/op0600761 | 1 |
Novel Synthetic Route of a Pivotal Intermediate for the Synthesis of 1β-Methyl Carbapenem Antibiotics | A novel synthetic method using an original and practical procedure for the preparation of the N -PNZ protected 2-aminomethylpyrrolidin-4-ylthio-containing side chain of doripenem hydrate ( S-4661 ), a new parenteral 1β-methylcarbapenem antibiotic, is described. trans -4-Hydroxy- l -proline was converted through an effi... | 10.1021/op0600714 | 1 |
Development of a Manufacturing Process for 1-(1-Pyridin-2-yl methyl-piperidin-4-yl)-1<i>H</i>-indole: A Key Intermediate for Protein Kinase C Inhibitor LY317615 | This contribution describes process development leading to the production of 1-(1-pyridin-2-yl methyl-piperidin-4-yl)-1 H -indole ( 11 ). The title compound 11 was produced via a Leimgruber−Batcho indole synthesis using key intermediates 2-(2,2-dimethoxyethyl)benzenamine ( 6 ) and, 1-(2-pyridinylmethyl)-4-piperidinone ... | 10.1021/op060068k | 1 |
Green Separation Processes: Fundamentals and Applications Edited by Carlos A. M. Afonso and Joao G. Crespo. Wiley-VCH: Weinheim. 2005. 363 pp. £100.00. ISBN 3-527-30985-3 | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTGreen Separation Processes: Fundamentals and Applications Edited by Carlos A. M. Afonso and Joao G. Crespo. Wiley-VCH: Weinheim. 2005. 363 pp. £100.00. ISBN 3-527-30985-3Peter L. SpargoView Author Information Scientific Update LLP, Maycroft Place, Stone Cross, Mayfield, E... | 10.1021/op060067s | 0 |
Open-Vessel Microwave-Promoted Suzuki Reactions Using Low Levels of Palladium Catalyst: Optimization and Scale-Up | Representative Suzuki couplings in water using low catalyst concentrations in conjunction with microwave heating have been transferred from sealed-vessel to open-vessel reaction conditions. They have then been scaled-up to the mole scale using a dedicated multimode microwave apparatus. The reactions are complete within... | 10.1021/op0600613 | 0 |
Development and Optimisation of an Unsymmetrical Hantzsch Reaction for Plant-Scale Manufacture | ( S )-3-(5-Oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinolin-4-yl)benzonitrile is a potassium-channel opener developed for the treatment of urinary urge incontinence. The key step in the synthesis is an unsymmetrical Hantzsch reaction to give a 2-hydroxy-1,2,3,4-tetrahydropyridine. In our study the order of additio... | 10.1021/op060057r | 1 |
A Green Process for Oxidation of <i>p</i>-Nitrotoluene Catalyzed by Metalloporphyrins under Mild Conditions | A novel synthetic technology of p -nitrobenzoic acid has been investigated with dioxygen by using metalloporphyrins RTPPM III Cl (M = Fe, Co, Mn) as biomimetic catalysts. Oxidation of p -nitrotoluene to p -nitrobenzoic acid under 2.0 MPa of O 2 in the presence of a microamount of metalloporphyrins (RTPPM III Cl) at 55 ... | 10.1021/op060056z | 0 |
Chlorination at the 8-Position of a Functionalized Quinolone and the Synthesis of Quinolone Antibiotic ABT-492 | The total synthesis of quinolone antibiotic ABT-492 has been achieved in 67% yield over nine steps from 2,4,5-trifluorobenzoic acid. The highlights of this synthesis include a novel chemoselective chlorination at the 8-position of a highly elaborated quinolone core. In addition, a Lewis acid promoted cyclization reacti... | 10.1021/op0600557 | 1 |
Synthesis of the Quinolone ABT-492: Crystallizations for Optimal Processing | ABT-492 has been under development at Abbott Laboratories as a quinolone antibiotic. A convergent syntheses was utilized to prepare the compound on a multi-kilogram scale. Difficulties in isolation of intermediates were overcome by developing control of the physical forms. Examples of controlling the agglomeration, cry... | 10.1021/op060054e | 1 |
A Practical Synthesis of 2-Arylamino-6-alkylaminopurines from 2,6-Dichloropurine | A practical synthesis of N -[4-(6-cyclobutylamino- 9H -purin-2-ylamino)-phenyl]- N -methyl acetamide (QAB205, 5a ), an antiasthmatic agent, is described from 2,6-dichloropurine ( 1 ) by base-assisted substitution of the 6-chloro substituent with cyclobutylamine ( 2a ) followed by a new trimethylsilyl chloride-catalyzed... | 10.1021/op060053m | 0 |
Catalyst Separation, Recovery and Recycling: Chemistry and Process Design Edited by D. Cole-Hamilton and R. Tooze. Springer: Dordrect. 2006. 250 pp. £96. ISBN 1-4020-4086-5. | null | 10.1021/op060050+ | 0 |
Chemical Development of ZD9331: Synthesis of a Bromomethylquinazolinone Avoiding a Nonselective Radical Bromination | An efficient regiospecific synthesis of ZD9331 Pivaloyloxymethyl (POM) Bromide ( 4 ) has been accomplished via ZD9331 Quinacetate HCl ( 15 ) avoiding a nonselective bromination. The original route used a radical bromination on a substrate with three methyl groups, which generated a range of bromomethyl derived compound... | 10.1021/op060049a | 1 |
Development of a Liquid-Phase Process for Recycling Resolving Agents within Diastereomeric Resolutions | This paper describes a liquid-phase process for recycling of resolving agents used in the diastereomeric resolution of chiral bases. The process is applicable to the resolution of any chiral base by an organic acid resolving agent which takes place in a polar solvent. The resolving agent is first of all separated from ... | 10.1021/op0600456 | 0 |
Safe and Practical Large-Scale Synthesis of 2-Aminoquinoline-6-Carboxylic Acid Benzyl Ester | An efficient three-step sequence has been developed for the synthesis of 2-aminoquinoline-6-carboxylic acid benzyl ester starting from commercially available 6-quinolinecarboxylic acid. The process features a novel and exceptionally mild conversion of a quinoline N -oxide to a 2-aminoquinoline using a triethylamine/amm... | 10.1021/op060044d | 1 |
Synthesis of Imidazole Based p38 MAP (Mitogen-Activated Protein) Kinase Inhibitors under Buffered Conditions | This article describes chemistry that was developed to give access to multigram quantities of imidazole 479754 and several related analogues for Eli Lilly's p38 MAPK program targeting therapies to address inflammation. The molecules of interest have an isopropyl sulfonyl group present on the 2-aminobenzimidazole hetero... | 10.1021/op060042t | 1 |
Enzymatic Process for the Synthesis of <i>cis/</i><i>trans</i>-(1<i>R</i>,5<i>R</i>)-Bicyclo[3.2.0]hept- 6-ylidene-acetate: Solvent Effect and NMR Study | An efficient enzymatic process has been developed to resolve a diastereomeric mixture of racemic ethyl bicyclo[3.2.0]hept-6-ylidene-acetate ( 1 ). Using 40% acetone, not only was the enantioselectivity of Candida antarctica lipase B (CAL-B) significantly improved to E > 200 from E = 2.7, remarkably the enzyme is able t... | 10.1021/op0600409 | 0 |
Process Modelling Tools for Continuous and Batch Organic Crystallization Processes Including Application to Scale-Up | Computational fluid dynamics (CFD) is a powerful simulation tool that was successfully used to investigate mixing, turbulence, and shear in a laboratory-scale MSMPR and batch cooling crystallizer for an organic fine chemical. CFD gives a qualitative engineering insight into the effects of the impeller configuration on ... | 10.1021/op060039+ | 0 |
A Scalable Synthesis of 1-Cytosinyl-<i>N</i>-malayamycin A: A Potent Fungicide | A stereocontrolled synthesis of 1-cytosinyl- N -malayamycin A, an N -analogue of the naturally occurring malayamycin A with fungicidal activity, is reported. The approach was designed to rely solely on substrate control for introduction of the required stereochemistry, avoiding the use of chiral reagents or auxiliaries... | 10.1021/op0600299 | 1 |
Analysis of Two-Liquid-Phase Multistep Biooxidation Based on a Process Model: Indications for Biological Energy Shortage | A process model for whole-cell biocatalysis in a two-liquid-phase system including cell growth and bioconversion kinetics was developed. The reaction considered is the kinetically controlled multistep oxidation of pseudocumene to 3,4-dimethylbenzaldehyde catalyzed by recombinant Escherichia coli expressing the Pseudomo... | 10.1021/op060028g | 0 |
An Efficient Multikilogram Synthesis of ABT-963: A Selective COX-2 Inhibitor | An efficient chemical process for the multikilogram synthesis of ABT-963 ( 3 ) is described. The potent and selective COX-2 inhibitor was prepared in four steps in 36% overall isolated yield from commercially available 3,4-difluoroaniline ( 4 ). The chemistry, which required no chromatography, involved a facile one-pot... | 10.1021/op060016v | 1 |
Synthesis of the CETP Inhibitor Torcetrapib: The Resolution Route and Origin of Stereoselectivity in the Iminium Ion Cyclization | A practical, efficient synthesis of (−)-(2 R,4 S )-4-[(3,5-bis-trifluoromethyl-benzyl)methoxycarbonylamino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester ( 1 ), a cholesteryl ester transfer protein (CETP) inhibitor, is described. The key reaction in the synthesis, addition of an N -vi... | 10.1021/op060014a | 1 |
Asymmetric Synthesis of the Cholesteryl Ester Transfer Protein Inhibitor Torcetrapib | Previously our group reported synthetic efforts used to synthesize kilogram quantities of the cholesteryl ester transfer protein (CETP) inhibitor torcetrapib, 1, via a mid-stage resolution. This account describes research conducted to develop an asymmetric route to this clinical candidate suitable for long-term manufac... | 10.1021/op060013i | 1 |
Efficient Enzymatic Process for the Production of (2 <i>S</i> )-4,4-Difluoro-3,3-dimethyl- <i>N</i> -Boc-proline, a Key Intermediate in the Synthesis of HIV Protease Inhibitors | (2 S )-4,4-Difluoro-3,3-dimethyl- N -Boc-proline ( 3 ) is a key intermediate for the synthesis of HIV protease inhibitors. Here, several approaches for the preparation of enantiopure 3 and its analogues are disclosed. Among these methods, one strategy relies on resolving the racemic methyl ester of 3 through a protease... | 10.1021/op060004+ | 0 |
Selective Lipase-Catalysed Hydrolysis of a 1,2-Diester in the Development of a New Route to AZD2563 DSP | During the development of a new route to AZD2563 DSP (DSP = disodium phosphate), a selective enzyme-catalysed hydrolysis of a 1,2-diester moiety to produce the secondary monoester was developed. Apart from two esters, the target molecule also contained three further functional groups prone to hydrolysis. A major challe... | 10.1021/op060003h | 1 |
An Effective Process for Conversion of Diphenylurea to CC-2, a Potential Decontaminant of Sulfur Mustard | N, N ‘-Dichlorobis(2,4,6-trichlorodiphenyl) urea, also known as 2-chlorocarbinol (CC-2) is a potential decontaminant of Sulfur Mustard (SM), which is also known as bis(2-chloroethyl) sulfide (HD), a well-known warfare agent. A new process has been developed for the synthesis of CC-2 from diphenylurea (DPU) through an i... | 10.1021/op060002p | 0 |
A Facile and Scaleable Synthesis of 3-<i>O</i>-Decladinose-6-methyl-10,11-dehydrate-erythromycin-3-one-2‘-acetate, an Important Intermediate for Ketolide Synthesis | A facile and scaleable synthetic process of compound 2, an important intermediate for synthesis of ketolide semisynthetic antibiotics, was developed starting from commercially available clathromycin with an overall yield of ∼74%. This synthetic pathway was composed of four steps from compound 3 which could be prepared ... | 10.1021/op060001x | 0 |
Modeling the Scale-Up of Contact Drying Processes | The conventional way of scaling up a contact drying process includes a pilot-scale step. Scaling up from lab scale to production scale without the use of a pilot plant saves time and money. A method has been developed to perform a scale-up from a 200-g bench-scale Rotavap drying process to production scale (approximate... | 10.1021/op058014i | 0 |
A Scalable Synthesis of <scp>l</scp>-Leucine-<i>N</i>-carboxyanhydride | Due to its relevance in the synthesis of well-defined oligopeptides, the l -leucine- N -carboxyanhydride (leucine-NCA) synthesis was selected for fine chemical scale-up with a scope on application on larger scales. The heterogeneous gas−solid−liquid nature of the leucine-NCA synthesis implied a mass transfer limited re... | 10.1021/op058009e | 0 |
Chemical Engineering, Trends and Developments Edited by Miguel A. Galan and Eva Martin del Valle. Wiley: Hoboken, NJ. 2005. 400 pp. $125.00/£65/99.90 Euro/160 SFR. ISBN: 0-470-02498-4. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewChemical Engineering, Trends and Developments Edited by Miguel A. Galan and Eva Martin del Valle. Wiley: Hoboken, NJ. 2005. 400 pp. $125.00/£65/99.90 Euro/160 SFR. ISBN: 0-470-02498-4.Francis McConvilleView Author Information FXM Engineering and Design, 6 Intervale Road, Worc... | 10.1021/op058008m | 0 |
Efficient Combination of Recyclable Task Specific Ionic Liquid and Microwave Dielectric Heating for the Synthesis of Lipophilic Esters | Mild and efficient esterification reactions of carboxylic acids with neo -pentanol were carried out using task-specific ionic liquids with hydrogen sulphate counteranion under microwave irradiation. The latent acidity of the ionic liquid was introduced by anion metathesis from hydrogen sulphate with the corresponding i... | 10.1021/op058002x | 0 |
First Scale-Up to Production Scale of a Ring Closing Metathesis Reaction Forming a 15-Membered Macrocycle as a Precursor of an Active Pharmaceutical Ingredient | BILN 2061 ZW ( 4 ) is a new chemical entity which shows promising results against the Hepatitis C virus. The major issue in the synthetic route represents the scale-up of a ring closing metathesis reaction to form a 15-membered macrocycle. The parameters chosen for the macrocyclization are discussed, and the experience... | 10.1021/op0580015 | 0 |
Development of a Large-Scale Synthesis of Sulphostin, a Dipeptidyl Peptidase IV Inhibitor | For the progress of the in vivo study on sulphostin, a dipeptidyl peptidase IV inhibitor, its large-scale synthetic method was investigated. The optical resolution of (3 S, RS P )-1-amino(sulfoamino)phosphinyl-3-benzyloxycarbonylamino-2-piperidin-one, which was the most difficult step in the previous method, was simpli... | 10.1021/op058000c | 1 |
Large-Scale Synthesis of (<i>R</i>)-2-Amino-1-(2-furyl)ethanol via a Chemoenzymatic Approach | A two-step chemoenzymatic synthesis of ( R )-2-amino-1-(2-furyl)ethanol for laboratory production was developed followed by successful up-scaling to kilogram scale. The generation of the asymmetric centre was accomplished by a highly enantioselective cyanohydrin reaction of furan-2-carbaldehyde with hydrocyanic acid ca... | 10.1021/op050264b | 1 |
Improved Practical Asymmetric Synthesis of α-Alkylmandelic Acids Utilizing Highly Diastereoselective Alkylation of 5-Aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones | A practical method for the synthesis of optically pure α-alkylmandelic acids 1 is described. The present improved robust method involved two reactions: a mild, convenient, stereoselective preparation of chiral cis -5-aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones, 9a − c, and highly diastereoselective alkylation of 9a − c, fo... | 10.1021/op050263j | 1 |
Optimization and Scale-Up of a Lipase-Catalyzed Enzymatic Resolution of an Indole Ester Intermediate for a Prostaglandin D<sub>2</sub>(DP) Receptor Antagonist Targeting Allergic Rhinitis | Pseudomonas fluorescens lipase was found to catalyze the asymmetric hydrolysis of racemic indole-ethyl ester 1. 1 The lipase converted the undesired (S) enantiomer to its corresponding acid, while leaving the desired (R) enantiomer untouched, yielding optically enhanced (R)- ester with an ee of 95% 1 at 48% conversion.... | 10.1021/op050261z | 0 |
Upscaling the Solid-Phase Synthesis of a Tetrahydrocarbazole in Chemical Development | A multigram solid-phase synthesis of tetrahydrocarbazole 1 was developed based a milligram-scale synthesis from Automated Medicinal Chemistry (Koppitz, M.; Reinhardt, G.; van Lingen, A. Tetrahedron Lett. 2005, 46, 911−914). It was shown that a fast scale-up by a factor of 2000 of the solid-phase synthesis is possible i... | 10.1021/op0502607 | 1 |
Good Pharmaceutical Manufacturing Practice: Rationale and Compliance By John Sharp. CRC Press: London, UK. 2005. 503 pp. List price $229.95 (Web price $207). ISBN 0-8493-1944-3. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewGood Pharmaceutical Manufacturing Practice: Rationale and Compliance By John Sharp. CRC Press: London, UK. 2005. 503 pp. List price $229.95 (Web price $207). ISBN 0-8493-1944-3.Derek RobinsonView Author Information 38 Millbrook Court, Little Mill, Pontypool, Monmouthshire NP4... | 10.1021/op0502598 | 0 |
Nitrilase-Catalysed Desymmetrisation of 3-Hydroxyglutaronitrile: Preparation of a Statin Side-Chain Intermediate | An efficient, scaleable synthesis of ethyl ( R )-4-cyano-3-hydroxybutyrate, a potential intermediate in the synthesis of Atorvastatin (Lipitor), has been developed. The three-stage process starts with reaction of low-cost epichlorohydrin with cyanide to give 3-hydroxyglutaronitrile (3-HGN). The second stage utilises a ... | 10.1021/op050257n | 1 |
Nearly Chromatography-Free Synthesis of the A<sub>3</sub>B-Porphyrin 5-(4-Hydroxymethylphenyl)-10,15,20-tri-<i>p</i>-tolylporphinatozinc(II) | Rational routes to synthetic porphyrins bearing distinct meso-substituents have typically been implemented at modest scale (<1 g quantities). The A 3 B-porphyrin 5-(4-hydroxymethylphenyl)-10,15,20-tri- p -tolylporphinatozinc(II) ( Zn-1 ) is required in multigram quantities for possible commercial use in information sto... | 10.1021/op0502553 | 1 |
Semiquantitative Process Screening for the Biocatalytic Synthesis of <scp>d</scp>-Xylulose-5-phosphate | In this paper we report a method of semiquantitative process screening or route scouting developed to reduce the number of potential process flowsheets for a multistep biocatalytic conversion. Using the dual-enzyme-based synthesis of d -xylulose- 5-phosphate as a model, a variety of possible processes was identified. U... | 10.1021/op050254a | 0 |
Novel Chemoenzymatic Protocol for the Synthesis of 3‘-<i>O</i>-Dimethoxytrityl-2‘-deoxynucleoside Derivatives as Building Blocks for Oligonucleotide Synthesis | An easy, efficient, and scalable chemoenzymatic strategy for the synthesis of 3‘- O -dimethoxytrityl-2‘-deoxynucleosides has been developed. A key feature of this approach is the regioselective synthesis of 5‘- O -levulinyl-2‘-deoxynucleosides through enzymatic acylation in the presence of Candida antarctica lipase B. ... | 10.1021/op050253i | 0 |
Development of an Efficient Synthesis of the Pyrrolquinolone PHA-529311 | An efficient synthesis of N -(4-chlorobenzyl)-2-(2-hydroxyethyl)-8-(morpholin-4-ylmethyl)-6-oxo-6H-pyrrol[3.2.1- ij ]quinoline-5-carboxamide ( 5 ) was developed. The route was chosen due to its reasonable length (seven steps), solubility of intermediates, and capabilities of the pilot and production facilities. The cri... | 10.1021/op050251y | 1 |
A Practical Synthesis of the Pseudotripeptide RC-1291 | The rapid process development of a scaleable synthesis of the pseudotripeptide RC-1291 for preclinical and clinical evaluation is described. By employing a nontraditional N -to- C coupling strategy, the peptide chain of RC-1291 was assembled in high yield, with minimal racemization and in an economical manner by introd... | 10.1021/op0502506 | 1 |
Handbook of Functionalized Organometallics: Applications in Synthesis (Volumes 1 and 2) Edited by P. Knochel. Wiley-VCH: Weinheim. 2005. £175. 652 + xix + 17 (index) pp. ISBN 3-527-31131-9. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTHandbook of Functionalized Organometallics: Applications in Synthesis (Volumes 1 and 2) Edited by P. Knochel. Wiley-VCH: Weinheim. 2005. £175. 652 + xix + 17 (index) pp. ISBN 3-527-31131-9.Cite this: Org. Process Res. Dev. 2006, 10, 4, 847Publication Date (Web):January 11... | 10.1021/op0502452 | 0 |
Development of a Scalable Synthetic Process for Selective Bromination of 4-Methyl-3,7-Substituted Coumarins | The hydroxyl-protected coumarin derivatives 6a − e of 4-methyl-3-(2,4-dihydroxyphenyl)-7-hydroxycoumarin ( 4 ) are key intermediates in the synthesis of unsymmetrical benzopyranobenzopyran compounds, a novel series of selective estrogen receptor modulators (SERMs). Free radical bromination of the 4-methyl group on 7-ac... | 10.1021/op050242p | 1 |
Development of a Scalable Synthesis to VEGFR Inhibitor AG-28262 | The synthesis of N,2-dimethyl-6-(2-(1-methyl-1 H -imidazol-2-yl)thieno[3,2- b ]pyridin-7-yloxy)benzo[ b ]thiophene-3-carboxamide ( 1, AG-28262) on kilogram scale is described. Initial syntheses of key components 2 and 3 worked well on laboratory scale but had significant drawbacks for larger-scale manufacture. Therefor... | 10.1021/op0502396 | 1 |
Towards an Information-Rich Process Development. Part I: Interfacing Experimentation with Qualitative/Semiquantitative Modelling | In today's competitive environment, the low-tonnage chemicals industry (fine and effect chemicals) is under increasing pressure to deliver more products to the market quicker and more cost effectively. Process development is a critical phase in bringing a fine chemical product from discovery to the market and requires ... | 10.1021/op050236t | 0 |
Regioselective Synthesis of an Imidazo[4,5-<i>c</i>]pyridine through Selective Acylation of 3,4-Diaminopyridine: Synthesis of CP-885,316 | CP-885,316 ( 1 ), an imidazo[4,5- c ]pyridine, 4, was prepared from 3,4-diaminopyridine ( 9 ). Two routes were demonstrated using the regioselective introduction of either an acetamide at the 3-position or a tert -butylcarbamate at the 4-position. | 10.1021/op0502250 | 1 |
Process Development of the Synthesis of 3,4,5-Trimethoxytoluene | 3,4,5-Trimethoxytoluene (TMT) was synthesized, starting from p -cresol, through bromination followed by methylation to give 3,5-dibromo-4-methoxytoluene (DBMT). The methoxylation of the latter with sodium methoxide in methanol was studied under pressure and by continuous distillation of the solvent, methanol. The O-met... | 10.1021/op0502248 | 0 |
A High Yield and Pilot-Scale Process for the Preparation of Adapalene | Strategies that were adopted during the process development of adapalene to achieve a cost-effective commercial-scale synthesis are described herein. These included (1) the use of AcOH/H 2 SO 4 to afford 2-(1-adamantyl)-4-bromophenol in quantitative yield; (2) the dimethyl sulfate methylation to enhance the yield of me... | 10.1021/op050223f | 1 |
A Concise, Efficient and Production-Scale Synthesis of a Protected <scp>l</scp>-Lyxonolactone Derivative: An Important Aldonolactone Core | A multikilogram-scale synthesis of l -lyxonolactone-2,3- O -isopropylidene is reported. It proceeds efficiently from an optimized, large-scale, aqueous bromine oxidation of d -ribose to d -ribonolactone including a one-pot isopropylidene formation, and subsequent conversion of the d -ribonolactone-2,3- O -isopropyliden... | 10.1021/op050222n | 0 |
Parameters Controlling the One-Step Derivatization of Controlled Pore Glass with a Diol for Solid-Phase Synthesis of 3‘-Modified Oligonucleotides | The one-step adsorption of oligoethylene glycol (OEG) affords an efficient derivatization of controlled pore glass (CPG) to perform oligonucleotide (ODN) solid-phase synthesis. This strategy leads to the synthesis of high-quality ODN-3‘-OEG. We have investigated various parameters that could influence the adsorption pr... | 10.1021/op050221v | 0 |
Practical Synthesis of 2-Amino-5-fluorothiazole Hydrochloride | The first synthesis of 2-amino-5-fluorothiazole hydrochloride is reported from 2-aminothiazole. The synthesis proceeds in 35% overall yield, involves no chromatographic purification, and has been employed to prepare multikilogram quantities of the title compound. The key fluorine-introducing step comprises the reaction... | 10.1021/op0502194 | 0 |
Selective Hydrolysis of Ethyl 5,6-Dihydro-4H-pyrrolo[1,2-<i>b</i>]pyrazole-2-carboxylate and Ethyl 5,6-Dihydro-4H-pyrrolo[1,2-<i>b</i>]pyrazole-3-carboxylate as a Key Step in the Large-Scale Synthesis of Bicyclic Heteroaryl Carboxyaldehydes | The isomeric mixture of ethyl 5,6-dihydro-4H-pyrrolo[1,2- b ]pyrazole-2- and −3-carboxylates ( 14 and 15 ), derived from a proline meso-ionic synthon, demonstrated remarkably different stabilities towards alkaline hydrolysis. On that basis, a nonchromatographic, highly efficient method for their large-scale separation ... | 10.1021/op050218b | 1 |
The Expedient Synthesis of 4,2‘-Difluoro-5‘-(7-trifluoromethyl- imidazo[1,2<i>-a</i>]pyrimidin-3-yl)biphenyl-2-carbonitrile, a GABA α2/3 Agonist | An expedient regioselective synthesis of a GABA α2/3 agonist 1 is described . The key step is an efficient regioselective palladium-catalyzed coupling of 7-trifluoromethylimidazo[1,2- a ]pyrimidine ( 5 ) to 5‘-chloro-4,2‘-difluorobiphenyl-2-carbonitrile ( 15 ). The efficiency of this step was affected by the choice of ... | 10.1021/op050217j | 1 |
(2-Acetoxyphenoxy)ethyl (APOE) as a Phosphate Protecting Group in Solid-Phase Synthesis of Oligonucleotides via the Phosphoramidite Approach | The (2-acetoxyphenoxy)ethyl (APOE) group could be an alternative to the conventional 2-cyanoethyl group for phosphate protection in solid-phase oligonucleotide synthesis to circumvent DNA alkylation by acrylonitrile generated under basic condition. This group is stable during oligonucleotide synthesis and can be remove... | 10.1021/op0502147 | 0 |
An Efficient Enantiopure Synthesis of a Pivotal Precursor to Substance P Antagonists<sup>1</sup> | Many substance P antagonists have a core structure based on the quinuclidine skeleton. Manufacture of these drug antagonists proceeds through the advanced intermediate (2 S,3 S )- cis -2-benzhydryl-3-aminoquinuclidine 1, and all previous syntheses of 2 S,3 S - 1 proceed through quinuclidinone 2 . The synthesis describe... | 10.1021/op050213e | 1 |
An Efficient and Economical Synthesis of 5,6-Diethyl-2,3-dihydro-1<i>H</i>-inden-2-amine Hydrochloride | An efficient and economical synthesis of 5,6-diethyl-2,3-dihydro-1 H -inden-2-amine hydrochloride ( 1 ) utilizing 2-aminoindan as a cheap and commercially readily available starting material is described. The newly developed synthesis involves six-steps with 49% overall yield, and it introduces two ethyl groups at the ... | 10.1021/op0502093 | 1 |
Isomerization-Free Sulfonylation and Its Application in the Synthesis of PHA-565272A | FeCl 3 catalyzed an isomerization-free Friedel−Crafts sulfonylation between 1-naphthalenesulfonyl chloride and halobenzenes. The coupled halide was then displaced using 35% hydrazine in DMSO to provide the Fischer indole precursor. Pure 5-chloro-2-pentanone was the key for a successful Grandberg modification of Fischer... | 10.1021/op050208a | 1 |
Development of a Pilot-Scale Preparation of <i>N</i>-[[(5S)-3-[4-(1,1-Dioxido-4- thiomorpholinyl)-3,5-difluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide, PNU-288034, an Oxazolidinone Antibacterial Agent | As part of Pfizer's continuing efforts in the oxazolidinone area, we have developed an efficient synthesis of PNU-288034 and successfully implemented it on pilot scale. The key step was a novel, acid-catalyzed, double Michael addition of 2,6-difluoroaniline with divinyl sulfone to install the desired dioxidothiomorphol... | 10.1021/op050207i | 1 |
Simple Preparation of Highly Pure Monomeric <i>ω</i>-Hydroxycarboxylic Acids | Highly pure monomeric ω -hydroxycarboxylic acids (HCAs) with ≥C 6 are prepared from their corresponding lactones or alkyl ω -hydroxycarboxylates through saponification followed by H 2 SO 4 acidification and treatment at 35−40 °C/8−12 mbar or by freeze-drying. The HCA is being formed through its sodium or potassium salt... | 10.1021/op0502046 | 0 |
Stereoselective Process for a CCR3 Antagonist | A convergent, multikilogram, stereoselective synthesis of 1 is described. A key fragment, ( S )-3-(4-fluorobenzyl)piperidine ( 2 ) was synthesized from valerolactam in three steps using our recently discovered Ir−BDPP-catalyzed asymmetric hydrogenation. Another key fragment, (1 R,2 R )-2-(benzyloxycarbonylamino)cyclohe... | 10.1021/op050202l | 1 |
<i>Special Feature Section: <u>Safety of Chemical Processes</u></i>Safety Feature | ADVERTISEMENT RETURN TO ISSUEPREVEditorialNEXTSpecial Feature Section: Safety of Chemical ProcessesSafety FeatureTrevor LairdView Author Information Editor Cite this: Org. Process Res. Dev. 2005, 9, 6, 951Publication Date (Web):October 26, 2005Publication History Published online26 October 2005Published inissue 1 Novem... | 10.1021/op050197l | 0 |
On Using Tree Analysis to Quantify the Material, Input Energy, and Cost Throughput Efficiencies of Simple and Complex Synthesis Plans and Networks: Towards a Blueprint for Quantitative Total Synthesis and Green Chemistry | Synthetic plans or networks may be depicted as trees in a graph-theoretical sense. When drawn in a systematic way according to a defined convention key “green” metrics relating to the efficiency of performance of a synthesis to a target molecule may be easily obtained by inspection, that is, by a “connect-the-dots” app... | 10.1021/op0501904 | 1 |
Understanding the Origin of Unusual Stepwise Hydrogenation Kinetics in the Synthesis of the 3-(4-Fluorophenyl)morpholine Moiety of NK<sub>1</sub> Receptor Antagonist Aprepitant | An efficient and highly stereoselective one-pot Grignard addition/hydrogenation procedure is a key step in the synthesis of the NK 1 receptor antagonist aprepitant. The critical influence of pH on the nature and stability of the intermediate Grignard adducts, along with their reactivity in the hydrogenation reaction, i... | 10.1021/op0501895 | 1 |
Handbook of Reagents for Organic Synthesis: Reagents for Glycoside, Nucleotide and Peptide Synthesis Edited by D. Crich. Wiley: New York. 2005. 770 + xiv pp. £80. ISBN 0-470-02304-X. | null | 10.1021/op050187k | 0 |
Calcium Pantothenate. Part 2.<sup>1</sup> Optimisation of Oxynitrilase-Catalysed Asymmetric Hydrocyanation of 3-Hydroxy-2,2-dimethylaldehyde: Synthesis of (<i>R</i>)-Pantolactone | The synthesis of ( R )-pantolactone via oxynitrilase-catalysed asymmetric hydrocyanation of 3-hydroxy-2,2-dimethylaldehyde has been investigated. ( R )-Oxynitrilases from almonds as well as from apple and plum kernels were employed as catalysts in the form of defatted meal. A number of factors influencing the hydrocyan... | 10.1021/op050186s | 1 |
A New and Direct Asymmetric Synthesis of a Hindered Chiral Amine via a Novel Sulfinate Ketimine Derived from <i>N</i>-Tosyl-1,2,3-oxathiazolidine-2-oxide: Practical Asymmetric Synthesis of (<i>R</i>)-Sibutramine | A novel and direct approach for the asymmetric synthesis of ( R )-sibutramine via chiral amine 5 using N -tosyl-1,2,3-oxathiazolidine-2-oxide ( 13 ) as a recyclable chiral auxiliary is described. Chiral sulfinate imine 16e was obtained by treatment of 13e with the imine intermediate formed from the reaction of a nitril... | 10.1021/op050182n | 1 |
Safety Improvement of Chemical Processes Involving Azides by Online Monitoring of the Hydrazoic Acid Concentration | Hydrazoic acid (HN 3 ) is formed during the synthesis of tributyltin azide and in the following cycloaddition to prepare a tetrazole ring compound. The formation of this substance is inherent to many azide processes because small amounts of protic components cannot be avoided. Hydrazoic acid is a very toxic volatile co... | 10.1021/op0501803 | 0 |
Development of a Practical High-Yield Industrial Synthesis of Pergolide Mesylate | The development of a high-yield and low environmental impact synthesis able to deliver highly pure pergolide mesylate 1 is described. The process [seven chemical steps (four telescoped), three steps of isolation of intermediate, and only one drying] affords pergolide mesylate 1 in 75−81% overall yield from dihydrolyser... | 10.1021/op0501747 | 1 |
A “Second-Generation Process” for the Synthesis of <scp>l</scp>-Neopentylglycine: Asymmetric Reductive Amination Using a Recombinant Whole Cell Catalyst | A “second-generation process” for the enantioselective synthesis of l -neopentylglycine has been developed, realizing the first whole cell-catalyzed approach to this pharmaceutically interesting, bulky amino acid. The synthesis of this nonnatural amino acid proceeds highly efficiently via a reductive amination of the c... | 10.1021/op0501702 | 0 |
Trouble with Potassium Carbonate and Centrifuges: Mass Transfer and Scale-Up Effects in the Manufacture of ZD9331 POM Quinacetate | Manufacture of ZD9331 pivaloyloxymethyl (POM) quinacetate, was progressively scaled up from large-scale lab to pilot plant to full-scale production. The specific surface area of the potassium carbonate used for the deprotonation was found to be critical as successive increases in the mass transfer area were counteracte... | 10.1021/op0501693 | 0 |
Development of a Scalable Process for a Key Intermediate of (<i>R</i>)-Metalaxyl by Enzymatic Kinetic Resolution | A scale-up study was carried out for the enzyme-catalyzed kinetic resolution of 2-methoxyethyl N -(2, 6)-dimethylphenyl)alaninate rac - 3 for the preparation of ( R )-metalaxyl at 20-L scale. Immobilization of lipase PS on a polymeric support enabled the reuse of the enzyme. The unreacted enantiomer was racemized by me... | 10.1021/op050166q | 0 |
A Practical Enantioselective Synthesis of a Novel Peptide Deformylase Inhibitor | A practical synthesis of the peptide deformylase inhibitor LBM415, (2 S )- N -(5-fluoro-1-oxido-2-pyridinyl)-1-[(2 R )-2-[(formylhydroxyamino)methyl]-1-oxohexyl]-2-pyrrolidinecarboxamide, magnesium salt 11, is described. The key chiral intermediate, (2 S )- N -(5-fluoro-2-pyridinyl)-1-[(2 R )-2-[[formyl(phenylmethoxy)a... | 10.1021/op050165y | 1 |
Process Analytical Technology Edited by Katherine A. Bakeev. Blackwell Publishing: Oxford. 2005. 451 pp. £109. ISBN 1-4051-2103-3. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTProcess Analytical Technology Edited by Katherine A. Bakeev. Blackwell Publishing: Oxford. 2005. 451 pp. £109. ISBN 1-4051-2103-3.Peter L. SpargoView Author Information Scientific Update LLP, Maycroft Place, Stone Cross, Mayfield, East Sussex TN20 6EW, United KingdomCite ... | 10.1021/op0501646 | 0 |
Handbook of Reagents for Organic Synthesis: Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis Edited by Peter Wipf. John Wiley & Sons Ltd: Chichester. 2005. 380 pp. £75. ISBN 0-470-86298-X (hardbound). | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTHandbook of Reagents for Organic Synthesis: Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis Edited by Peter Wipf. John Wiley & Sons Ltd: Chichester. 2005. 380 pp. £75. ISBN 0-470-86298-X (hardbound).Peter L. SpargoView Author Information Scie... | 10.1021/op050163d | 0 |
The Synthesis of a Novel Inhibitor of B-Raf Kinase | A scaleable synthetic route to [4,7‘]bis-isoquinolinyl-1-yl-(2- tert -butyl-pyrimidine-5-yl)amine ( 1 ), an inhibitor of B-Raf kinase is described. The key step in the synthesis is the Pd-catalyzed Negishi coupling of 4-bromo-1-chloroisoquinoline with trifluoromethanesulfonic acid isoquinoline-7-yl ester to yield 1-chl... | 10.1021/op0501601 | 1 |
A Practical Method for the Synthesis of a Cyclosporine−Fluorescein Conjugate | A straightforward synthesis of a cyclosporine−fluorescein conjugate through the MeBmt hydroxyl group was developed. Reaction of cyclosporine A in phosgene/toluene solution with added triethylamine, followed by subsequent reaction with 4‘-aminomethylfluorescein, produces good yields of the cyclosporine−fluorescein conju... | 10.1021/op0501592 | 0 |
Oxazoles: Synthesis, Reactions and Spectroscopy, Part A Edited by D. C. Palmer. Wiley-Interscience: Hoboken, NJ. 2003. 640 + xviii pp. £195. ISBN 0-473-39494-7. | null | 10.1021/op050158+ | 0 |
Experiences with Commercial Production Scale Operation of Dissolving Metal Reduction Using Lithium Metal and Liquid Ammonia | The final step which generates free base in the synthesis of Sumanirole Maleate (PNU-95666E) consists of a cryogenic dissolving metal reduction using lithium metal and liquid ammonia. This chemistry was new to the Pfizer API production plant. Due to the hazards associated with the handling of lithium metal and ammonia ... | 10.1021/op050155x | 0 |
One-Pot Preparation of 7-Hydroxyquinoline | An efficient one-pot procedure for the four-step preparation of 7-hydroxyquinoline ( 1 ) from 3- N -tosylaminophenol ( 4 ) in 60% isolated yield, that reduces the risk of exposure to acrolein ( 2 ), is described. | 10.1021/op0501545 | 0 |
A New Efficient Stereoselective Debromination Reaction with Trialkylgermanium Hydrides Useful in the Design of Short Synthetic Routes to β-Lactamase Inhibitor Prodrugs | Prodrugs derived from the β-lactamase inhibitor 6-β-hydroxymethylsulbactam can be synthesized efficiently in a three-step process by making use of the highly stereoselective radical debromination utilizing tri- n -butylgermanium hydride. This reagent is capable of abstracting bromine from the C-6 position of pairs of e... | 10.1021/op050151s | 1 |
Contemporary Drug Synthesis By Jie Jack Li, Douglas S. Johnson, Drago R. Sliskovic, and Bruce D. Roth. Wiley-Interscience: New Jersey. 2004. 221 pp. £51.50. ISBN 0-471-21480-9. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTContemporary Drug Synthesis By Jie Jack Li, Douglas S. Johnson, Drago R. Sliskovic, and Bruce D. Roth. Wiley-Interscience: New Jersey. 2004. 221 pp. £51.50. ISBN 0-471-21480-9.Peter L. SpargoView Author Information Scientific Update LLP, Maycroft Place, Stone Cross, Mayfi... | 10.1021/op0501489 | 0 |
Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Second Revised and Enlarged Edition. (2-Volume Set.) Edited by Matthias Beller and Carsten Bolm. Wiley-VCH: Weinheim. 2004. 662 pp. (Vol. 1), 652 pp (Vol. 2). £270. ISBN 3-527-30613-7. | ADVERTISEMENT RETURN TO ISSUEPREVBook ReviewNEXTTransition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Second Revised and Enlarged Edition. (2-Volume Set.) Edited by Matthias Beller and Carsten Bolm. Wiley-VCH: Weinheim. 2004. 662 pp. (Vol. 1), 652 pp (Vol. 2). £270. ISBN 3-527-30613-7.Peter L. Sp... | 10.1021/op050145w | 0 |
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