Table of Contents

July 17, 2009
Volume 13, Issue 4
Pages 659-822

In this issue:

About the Cover:

Photograph and inset of a 30-liter glass pilot-plant distillation system. Copyright © 2001 BüchiGlassUster. Reproduced with permission.

For Selected Content:

Editorial

Octavio Augusto Ceva Antunes

Trevor Laird
p 659
Publication Date (Web): July 17, 2009 (Editorial)
DOI: 10.1021/op900147e

Highlights from the Literature

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

Mark McLaughlin, Silvina GarcaRubio, Matthew Pfeiffer, Ulf Tilstam, Andrei A. Zlota, Trevor Laird
pp 660–668
Publication Date (Web): July 17, 2009 (Highlights from the Literature)
DOI: 10.1021/op9001565

Highlights from the Patents

A Review of U.S. Patents in the Field of Organic Process Development Published During February and March 2009

Keith Turner
pp 669–682
Publication Date (Web): July 17, 2009 (Highlights From Patents)
DOI: 10.1021/op900144u

Concept Article

Preparative Chromatography Technique in the Removal of Isostructural Genotoxic Impurity in Rizatriptan: Use of Physicochemical Descriptors of Solute and Adsorbent

Srinivasula Reddy Maddula, Manoj Kharkar, Kushal Manudhane, Sandeep Kale, Abijar Bhori, Arvind Lali, P. K. Dubey, K. R. Janardana Sarma, Apurba Bhattacharya and Rakeshwar Bandichhor
pp 683–689
Publication Date (Web): May 18, 2009 (Concept Article)
DOI: 10.1021/op9000093

Full Papers

Model-Based Solvent Selection during Conceptual Process Design of a New Drug Manufacturing Process

Daniel Hsieh, Alexander J. Marchut, Chenkou Wei, Bin Zheng, Steve S. Y. Wang and San Kiang
pp 690–697
Publication Date (Web): July 2, 2009 (Article)
DOI: 10.1021/op900058e

Facile, Fast and Safe Process Development of Nitration and Bromination Reactions Using Continuous Flow Reactors

Jacques Pelleter and Fabrice Renaud
pp 698–705
Publication Date (Web): May 7, 2009 (Article)
DOI: 10.1021/op8002695

Development of an Acid-Washable Tag for the Separation of Enantiomers from Bioresolutions

Maude Brossat, Thomas S. Moody, Florian de Nanteuil, Stephen J. C. Taylor and Fatima Vaughan
pp 706–709
Publication Date (Web): May 18, 2009 (Article)
DOI: 10.1021/op900028d

A Facile, One-Pot Synthesis of Lacidipine Using in Situ Generation of Wittig Intermediates

V. V. N. K. V. Prasada Raju, Vedantham Ravindra, Vijayavitthal T. Mathad, P. K. Dubey and Padi Pratap Reddy
pp 710–715
Publication Date (Web): May 19, 2009 (Article)
DOI: 10.1021/op900055u

The Process Development of Ravuconazole: An Efficient Multikilogram Scale Preparation of an Antifungal Agent

Jaan Pesti, Chien-Kuang Chen, Lori Spangler, Albert J. DelMonte, Serge Benoit, Derek Berglund, Jeffrey Bien, Paul Brodfuehrer, Yeung Chan, Elisabeth Corbett, Carrie Costello, Paul DeMena, Robert P. Discordia, Wendel Doubleday, Zhinong Gao, Stephane Gingras, John Grosso, Oscar Haas, David Kacsur, Chiajen Lai, Simon Leung, Melanie Miller, Jale Muslehiddinoglu, Nina Nguyen, Jun Qiu, Martina Olzog, Emily Reiff, Dominique Thoraval, Michael Totleben, Dale Vanyo, Purushotham Vemishetti, John Wasylak and Chenkou Wei
pp 716–728
Publication Date (Web): July 17, 2009 (Article)
DOI: 10.1021/op900065c

Process Development for A Novel Pleuromutilin-Derived Antibiotic

Yemane Andemichael, Jun Chen, Jacalyn S. Clawson, Wenning Dai, Ann Diederich, Susan V. Downing, Alan J. Freyer, Peng Liu, Lynette M. Oh, Daniel B. Patience, Sonja Sharpe, Joseph Sisko, Julie Tsui, Frederick G. Vogt, Jun Wang, Lori Wernersbach, Edward C. Webb, James Wertman and Leon Zhou
pp 729–738
Publication Date (Web): July 2, 2009 (Article)
DOI: 10.1021/op900104g

Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(S)-4-[Bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]-4-(carboxy-kO)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography

Pier Lucio Anelli, Marino Brocchetta, Luciano Lattuada, Giuseppe Manfredi, Pierfrancesco Morosini, Marcella Murru, Daniela Palano, Marco Sipioni and Massimo Visigalli
pp 739–746
Publication Date (Web): May 22, 2009 (Article)
DOI: 10.1021/op900008a

Adaptation of an Exothermic and Acylazide-Involving Synthesis Sequence to Microreactor Technology

Luigi Rumi, Christophe Pfleger, Paul Spurr, Uwe Klinkhammer and Willi Bannwarth
pp 747–750
Publication Date (Web): May 20, 2009 (Article)
DOI: 10.1021/op9000516

A Convergent Synthesis of AR-C123196 Utilising Reaction Between a Cyclic Carbonate and a Phenol for Aryl Alkyl Ether Formation

Glyn L. Allsop, Andrea J. Cole, Melvyn E. Giles, Eric Merifield, Allison J. Noble, Michael A. Pritchett, Lindsay A. Purdie and John T. Singleton
pp 751–759
Publication Date (Web): June 9, 2009 (Article)
DOI: 10.1021/op9000687

Practical Synthetic Method of (2Z,3E)-1,4-Diphenylbutadiene T-2639, an Inhibitor of Plasminogen Activator Inhibitor-1 (PAI-1) Production

Hiroshi Miyazaki, Hiroshi Ohmizu and Tsuyoshi Ogiku
pp 760–763
Publication Date (Web): May 28, 2009 (Article)
DOI: 10.1021/op9000719

Development of an Open-Air and Robust Method for Large-Scale Palladium-Catalyzed Cyanation of Aryl Halides: The Use of i-PrOH to Prevent Catalyst Poisoning by Oxygen

Yunlai Ren, Zhifei Liu, Shebin He, Shuang Zhao, Jianji Wang, Ruiqi Niu and Weiping Yin
pp 764–768
Publication Date (Web): May 14, 2009 (Article)
DOI: 10.1021/op9000725

A Simple, Efficient, Green, Cost Effective and Chemoselective Process for the Esterification of Carboxylic Acids

Vamsi V. Rekha, Modukuri V. Ramani, A. Ratnamala, Vempati Rupakalpana, Gottumukkala V. Subbaraju, Chava Satyanarayana and C. Someswara Rao
pp 769–773
Publication Date (Web): July 2, 2009 (Article)
DOI: 10.1021/op900096y

Development of a Supply Route for the Synthesis of an iNOS Inhibitor: Complications of the Key SN2 Reaction

Geracimos Rassias, Stephen A. Hermitage, Mahesh J. Sanganee, Peter M. Kincey, Neil M. Smith, Ian P. Andrews, Gary T. Borrett and Graham R. Slater
pp 774–780
Publication Date (Web): July 2, 2009 (Article)
DOI: 10.1021/op900108b

Communications to the Editor

Kilogram-Scale Synthesis of the CXCR4 Antagonist GSK812397

Sharon Boggs, Vassil I. Elitzin, Kristjan Gudmundsson, Michael T. Martin and Matthew J. Sharp
pp 781–785
Publication Date (Web): May 7, 2009 (Communication to Editor)
DOI: 10.1021/op9000675

Controlling the Genotoxins Ethyl Chloride and Methyl Chloride Formed During the Preparation of Amine Hydrochloride Salts from Solutions of Ethanol and Methanol

Qiang Yang, Brian P. Haney, Alexander Vaux, Dean A. Riley, Linda Heidrich, Ping He, Paul Mason, Ashok Tehim, Lawrence E. Fisher, Hans Maag and Neal G. Anderson
pp 786–791
Publication Date (Web): June 8, 2009 (Communication to Editor)
DOI: 10.1021/op9000737

An Improved and Single Pot Process for the Production of Quetiapine Hemifumarate Substantially Free from Potential Impurities

Navnath C. Niphade, Anil C. Mali, Bhushan S. Pandit, Kunal M. Jagtap, Sanjay A. Jadhav, Madhukar N. Jachak and Vijayavitthal T. Mathad
pp 792–797
Publication Date (Web): June 23, 2009 (Communication to Editor)
DOI: 10.1021/op900097q

Lecture Transcripts

Orthogonal Experiments in the Development of Organic Synthetic Processes

Rolf Carlson, Geir Simonsen and Alexandre Descomps, Johan E. Carlson
pp 798–803
Publication Date (Web): May 7, 2009 (Lecture Transcript)
DOI: 10.1021/op800322h

Technical Notes

An Improved Synthesis of Antiulcerative Drug: Tenatoprazole

Somaiah Sripathi, Ramachandra Reddy Bojja, Venugopal Reddy Karnati, V. V. N. K. V. Prasada Raju and Mayur D. Khunt
pp 804–806
Publication Date (Web): November 12, 2008 (Technical Note)
DOI: 10.1021/op800173u

Practical Synthesis of 5-Fluoro-2-(piperidin-4-yloxy)pyrimidin-4-amine, a Key Intermediate in the Preparation of Potent Deoxycytidine Kinase Inhibitors

Haiming Zhang, Jie Yan, Ramanaiah C. Kanamarlapudi, Wenxue Wu and Philip Keyes
pp 807–811
Publication Date (Web): April 30, 2009 (Technical Note)
DOI: 10.1021/op900060u

An Efficient Process of Racemization of 3-(Carbamoylmethyl)-5-methylhexanoic acid: A Pregabalin Intermediate

Anil B. Chavan, Golak C. Maikap and Mukund K. Gurjar
pp 812–814
Publication Date (Web): May 18, 2009 (Technical Note)
DOI: 10.1021/op900064x

An Improved Process for the Preparation of Diphenylmethyl 7β-Phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate

Keping Yu, Nan Sun, Shanzong Fang, Weimin Mo, Baoxiang Hu, Zhenlu Shen and Xinquan Hu
pp 815–819
Publication Date (Web): May 28, 2009 (Technical Note)
DOI: 10.1021/op900063e

First Multigram Preparation of SCP-123, A Novel Water-Soluble Analgesic

Lei Miao, Liang Xu, Kenneth W. Narducy and Mark L. Trudell
pp 820–822
Publication Date (Web): June 25, 2009 (Technical Note)
DOI: 10.1021/op900113b