Table of Contents

September 2003
Volume 7, Issue 5
Pages 613-774

Editorial

The “Bookworm” Has Turned ...

Trevor Laird
p 613
Publication Date (Web): September 19, 2003 (Editorial)
DOI: 10.1021/op034113p

Highlights from the Literature

Some Items of Interest to Process R&D Chemists and Engineers

pp 614–621
Publication Date (Web): September 19, 2003 (Editorial)
DOI: 10.1021/op034114h

Reviews

Concepts of Nature in Organic Synthesis:  Cascade Catalysis and Multistep Conversions in Concert

Alle Bruggink, Rob Schoevaart,§ and Tom Kieboom*§
pp 622–640
Publication Date (Web): August 16, 2003 (Review)
DOI: 10.1021/op0340311

Articles

Highly Chemoselective Heterogeneous Pd-Catalyzed Biaryl Synthesis from Haloarenes:  Reaction in an Oil-in-Water Microemulsion

Sudip Mukhopadhyay,* Anan Yaghmur, Mubeen Baidossi, Buddhadeb Kundu,§ and Yoel Sasson*
pp 641–643
Publication Date (Web): August 07, 2003 (Article)
DOI: 10.1021/op020094s

A Scalable Synthesis of (R)-3,5-Dihydro-4H-dinaphth[2,1-c:1‘2‘-e]azepine

Masaya Ikunaka,* Keiji Maruoka,* Yoshiaki Okuda,§ and Takashi Ooi
pp 644–648
Publication Date (Web): August 01, 2003 (Article)
DOI: 10.1021/op034067t

Practical Large-Scale Synthesis of the 2-Aminomethylpyrrolidin-4-ylthio-Containing Side Chain of the Novel Carbapenem Antibiotic Doripenem

Yutaka Nishino, Tadafumi Komurasaki, Tetsuya Yuasa, Makoto Kakinuma, Kenji Izumi, Makoto Kobayashi, Shinichiro Fujiie, Teruhiro Gotoh, Yoshiyuki Masui,* Makoto Hajima, Masayuki Takahira,§ Akira Okuyama, and Takahiro Kataoka
pp 649–654
Publication Date (Web): June 06, 2003 (Article)
DOI: 10.1021/op0340412

The Development of a Manufacturing Route for the GPIIb/IIIa Receptor Antagonist SB-214857-A. Part 1:  Synthesis of the Key Intermediate 2,3,4,5-Tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetic Acid Methyl Ester, SB-235349

Ian P. Andrews, Richard J. Atkins, Gary F. Breen, John S. Carey, Michael A. Forth, David O. Morgan,* Amin Shamji, Andrew C. Share, Stephen A. C. Smith, Timothy C. Walsgrove, and Andrew S. Wells
pp 655–662
Publication Date (Web): July 26, 2003 (Article)
DOI: 10.1021/op034024c

The Development of a Manufacturing Route for the GPIIb/IIIa Receptor Antagonist SB-214857-A. Part 2:  Conversion of the Key Intermediate SB-235349 to SB-214857-A

Richard J. Atkins, Adam Banks, Richard K. Bellingham, Gary F. Breen, John S. Carey,* Stephen K. Etridge, Jerome F. Hayes, Nigel Hussain, David O. Morgan, Paul Oxley, Stephen C. Passey, Timothy C. Walsgrove, and Andrew S. Wells
pp 663–675
Publication Date (Web): July 26, 2003 (Article)
DOI: 10.1021/op034023k

Cross-Coupling Methods for the Large-Scale Preparation of an Imidazole−Thienopyridine:  Synthesis of [2-(3-Methyl-3H-imidazol-4-yl)- thieno[3,2-b]pyridin-7-yl]-(2-methyl-1H-indol-5-yl)-amine

J. A. Ragan,* J. W. Raggon, P. D. Hill, B. P. Jones, R. E. McDermott, M. J. Munchhof, M. A. Marx, J. M. Casavant, B. A. Cooper, J. L. Doty, and Y. Lu
pp 676–683
Publication Date (Web): August 01, 2003 (Article)
DOI: 10.1021/op0340457

Reactions in Closed Batch Reactors, Operational and Safety Issues:  A Model To Predict How Degree of Filling and Rate of Heating Affect Reaction Times and Buildup of Internal Pressure

Guido Galliani, Marco Orlandi, and Bruno Rindone*
pp 684–691
Publication Date (Web): July 10, 2003 (Article)
DOI: 10.1021/op0340098

An Efficient One-Pot Process for 10-Bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one, an Intermediate to SCH 66336

Xiaoyong Fu,* Timothy L. McAllister, Xiongwei Shi, T. K. Thiruvengadam, Chou-Hong Tann, and Junning Lee
pp 692–695
Publication Date (Web): August 12, 2003 (Article)
DOI: 10.1021/op034054f

An Improved Method for the Palladium Cross-Coupling Reaction of Oxazol-2-ylzinc Derivatives with Aryl Bromides

Michael R. Reeder,* Harold E. Gleaves, Sheree A. Hoover, Rick J. Imbordino, and Jeffrey J. Pangborn
pp 696–699
Publication Date (Web): August 13, 2003 (Article)
DOI: 10.1021/op034059c

The Process Development of a Novel Aldose Reductase Inhibitor, FK366. Part 1. Improvement of Discovery Process and New Syntheses of 1-Substituted Quinazolinediones

Shunsuke Goto,* Hiroyuki Tsuboi, Masami Kanoda, Koji Mukai, and Kooji Kagara
pp 700–706
Publication Date (Web): August 20, 2003 (Article)
DOI: 10.1021/op0340661

Scalability of Microwave-Assisted Organic Synthesis. From Single-Mode to Multimode Parallel Batch Reactors

Alexander Stadler, Behrooz H. Yousefi, Doris Dallinger, Peter Walla, Erik Van der Eycken, Nadya Kaval, and C. Oliver Kappe*
pp 707–716
Publication Date (Web): August 09, 2003 (Article)
DOI: 10.1021/op034075+

Temperature Selective Diastereo-Recognition (TSD):  Enantiomeric Ibuprofen via Environmentally Benign Selective Crystallization

Apurba Bhattacharya*David Murphy
pp 717–722
Publication Date (Web): August 02, 2003 (Article)
DOI: 10.1021/op030203i

Design of New Reaction Conditions for the Sugasawa Reaction Based on Mechanistic Insights

Kapa Prasad,* George T. Lee, Apurva Chaudhary, Michael J. Girgis, James W. Streemke, and Oljan Repi
pp 723–732
Publication Date (Web): August 01, 2003 (Article)
DOI: 10.1021/op0340659

A Practical Synthesis of 6-[2-(2,5-Dimethoxyphenyl)ethyl]-4-ethylquinazoline and the Art of Removing Palladium from the Products of Pd-Catalyzed Reactions

Kurt Königsberger, Guang-Pei Chen, Raeann R. Wu, Michael J. Girgis, Kapa Prasad,* Oljan Repi, and Thomas J. Blacklock
pp 733–742
Publication Date (Web): August 20, 2003 (Article)
DOI: 10.1021/op034072x

Kinetically Controlled Diastereoselective Synthesis of CPS124, a Carnitine Monothiophosphate

Kapa Prasad,* David D. Xu, Orin Tempkin, Edwin B. Villhauer, and Oljan Repi
pp 743–749
Publication Date (Web): July 31, 2003 (Article)
DOI: 10.1021/op034064g

Technical Notes

Isolation and Identification of the Major Extractable Impurity from Dowex 1×2 Resin

Jacob S. Tou,* James G. Kostelc, Michael R. Schlittler, and Bernard N. Violand
pp 750–753
Publication Date (Web): July 25, 2003 (Technical Note)
DOI: 10.1021/op034044e

A Novel Method for the Direct Sulfonation of CH4 with SO3 in the Presence of KO2 and a Promoter

Sudip Mukhopadhyay and Alexis T. Bell*
pp 754–757
Publication Date (Web): August 07, 2003 (Technical Note)
DOI: 10.1021/op0300140

Identification and Control of a Process-Related Impurity in the Chlorination of 3-Hydroxy-3-carbacephem

Yatendra Kumar,* Neera Tewari, Hashim Nizar, Bishwa Prakash Rai, and Shailendra Kumar Singh
pp 758–761
Publication Date (Web): May 15, 2003 (Technical Note)
DOI: 10.1021/op034026x

Technology Reports

Continuous-Flow Generation of Anhydrous Diazonium Species:  Monolithic Microfluidic Reactors for the Chemistry of Unstable Intermediates

Robin Fortt, Robert C. R. Wootton, and Andrew J. de Mello*
pp 762–768
Publication Date (Web): May 31, 2003 (Technology Report)
DOI: 10.1021/op025586j

Kinetics of Liquid-Phase Catalytic Hydrogenation of Benzophenone to Benzhydrol

Sunil P. Bawane and Sudhirprakash B. Sawant*
pp 769–773
Publication Date (Web): July 24, 2003 (Technology Report)
DOI: 10.1021/op030016k

Additions & Corrections

A Review of U.S. Patents in the Field of Organic Process Development Published during December 2002 through March 2003

Keith Turner
p 774
Publication Date (Web): August 22, 2003 (Addition/Correction)
DOI: 10.1021/op0300342