Table of Contents

May 15, 2009
Volume 13, Issue 3
Pages 363-657

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

Genotoxic Impurities

Trevor Laird
p 363
Publication Date (Web): April 24, 2009 (Editorial)
DOI: 10.1021/op900098m

Highlights from the Literature

Some Items of Interest to Process Chemists and Engineers

Mark McLaughlin, Matthew Pfeiffer, Ulf Tilstam, Trevor Laird, Andrei Zlota
pp 364–370
Publication Date (Web): May 15, 2009 (Highlights from the Literature)
DOI: 10.1021/op9001005

Highlights from the Patents

A Review of U.S. Patents in the Field of Organic Process Development Published During October and November 2008

Keith Turner
pp 371–380
Publication Date (Web): April 10, 2009 (Highlights From Patents)
DOI: 10.1021/op900077k

A Review of U.S. Patents in the Field of Organic Process Development Published During December 2008 and January 2009

Keith Turner
pp 381–390
Publication Date (Web): April 22, 2009 (Highlights From Patents)
DOI: 10.1021/op9000884

Regulatory Highlights

Regulatory Highlights for September 2008 to February 2009

Derek Robinson
pp 391–396
Publication Date (Web): April 2, 2009 (Regulatory Highlights)
DOI: 10.1021/op900033d

Green Chemistry Highlights

Green Chemistry Articles of Interest to the Pharmaceutical Industry

Ian Andrews, Jian Cui, Jimmy DaSilva, Leo Dudin, Peter Dunn, John Hayler, Bill Hinkley, David Hughes, Bernard Kaptein, Stanley Kolis, Kurt Lorenz, Suju Mathew, Thomas Rammeloo, Lijun Wang, Andrew Wells, Timothy White, Chaoyu Xie, Fuyao Zhang
pp 397–408
Publication Date (Web): May 15, 2009 (Green Chemistry Highlights)
DOI: 10.1021/op900082k

Letter to the Editor

Full Papers

An Efficient Catalytic Method for the Beckmann Rearrangement of Ketoximes to Lactams by Cyanuric Chloride and Phosphazene Catalysts

Masaharu Hashimoto, Yasushi Obora and Yasutaka Ishii
pp 411–414
Publication Date (Web): January 6, 2009 (Article)
DOI: 10.1021/op800258s
Figure 1 of 3

A Scalable, Enantioselective Synthesis of the α2-Adrenergic Agonist, Lofexidine

Ashish P. Vartak and Peter A. Crooks
pp 415–419
Publication Date (Web): January 8, 2009 (Article)
DOI: 10.1021/op8002689
Figure 1 of 2

Reaction Progress Analysis: Powerful Tool for Understanding Suzuki−Miyaura Reaction and Control of Polychlorobiphenyl Impurity

Sandeep B. Kedia and Mark B. Mitchell
pp 420–428
Publication Date (Web): January 20, 2009 (Article)
DOI: 10.1021/op800205x
Figure 1 of 16

Mechanism and Processing Parameters Affecting the Formation of Methyl Methanesulfonate from Methanol and Methanesulfonic Acid: An Illustrative Example for Sulfonate Ester Impurity Formation

Andrew Teasdale, Stephen C. Eyley, Ed Delaney, Karine Jacq, Karen Taylor-Worth, Andrew Lipczynski, Van Reif, David P. Elder, Kevin L. Facchine, Simon Golec, Rolf Schulte Oestrich, Pat Sandra and Frank David
pp 429–433
Publication Date (Web): January 14, 2009 (Article)
DOI: 10.1021/op800192a
Figure 1 of 6

A New Approach to the Synthesis of 4-Hydroxyethylsulfonylstyrene

Christophe Grosjean, Andrew P. Henderson, Damien Hrault, Gennadiy Ilyashenko, Jonathan P. Knowles, Andrew Whiting and Allen R. Wright
pp 434–441
Publication Date (Web): January 20, 2009 (Article)
DOI: 10.1021/op800292b
Figure 1 of 3

Practical Syntheses of Oxindole Derivatives: Chemical Development towards 2-(5-Chloro-2-oxo-2,3-dihydroindol-1-yl)acetamide and (S)-2-(5-Chloro-2-oxo-2,3-dihydroindol-1-yl)propionamide

Fabienne Broeders, Laurent Defrre, Marie-France Deltent, Frank Driessens, Frdric Gilson, Luc Grooters, Xavier Ikonomakos, Frdric Limauge, Emmanuel Sergeef and Natacha Verstraeten
pp 442–449
Publication Date (Web): January 30, 2009 (Article)
DOI: 10.1021/op800203p
Figure 1 of 7

A Novel Method for Large-Scale Synthesis of Lamivudine through Cocrystal Formation of Racemic Lamivudine with (S)-(−)-1,1′-Bi(2-naphthol) [(S)-(BINOL)]

Bhairab Nath Roy, Girij Pal Singh, Dhananjai Srivastava, Harishchandra S. Jadhav, Manmeet B. Saini and Umesh P. Aher
pp 450–455
Publication Date (Web): January 21, 2009 (Article)
DOI: 10.1021/op800228h
Figure 1 of 2

Development of Scaffold Synthesis for the Preparation of New Insulin-Like Growth Factor 1 Receptor Inhibitors

Ilaria Candiani, Germano D’Arasmo, Franco Heidempergher and Attilio Tomasi
pp 456–462
Publication Date (Web): January 21, 2009 (Article)
DOI: 10.1021/op8002536
Figure 1 of 5

Efficient Synthesis of (2S,3S)-2-Ethyl-3-methylvaleramide Using (1S,2S)-Pseudoephedrine as a Chiral Auxiliary

Bin-Feng Li, Robert M. Hughes, Jackie Le, Kevin McGee, Donald J. Gallagher, Raymond S. Gross, David Provencal, Jayachandra P. Reddy, Peng Wang, Lev Zegelman, Yuxin Zhao and Scott E. Zook
pp 463–467
Publication Date (Web): January 30, 2009 (Article)
DOI: 10.1021/op800260j

An Investigation into the Formation of Impurity B during the Optimization of Naratriptan Hydrochloride

U. Sampath Kumar, V. Ravi Sankar, S. Bharani Kumar, M. Pandi Prabhu and S. Mahender Rao
pp 468–470
Publication Date (Web): January 28, 2009 (Article)
DOI: 10.1021/op800286f

Development of a Sequential Tetrahydropyran and Tertiary Butyl Deprotection: High-Throughput Experimentation, Mechanistic Analysis, and DOE Optimization

Jeffrey T. Kuethe, David M. Tellers, Steven A. Weissman and Nobuyoshi Yasuda
pp 471–477
Publication Date (Web): March 2, 2009 (Article)
DOI: 10.1021/op8002739
Figure 1 of 6

Scalable Non-Aqueous Process to Prepare Water Soluble 3-Amino-pentan-1,5-diol

Thimma Rawalpally, Yaohui Ji, Thomas Cleary and Billy Edwards
pp 478–482
Publication Date (Web): February 13, 2009 (Article)
DOI: 10.1021/op800245v

Enzymatic Desymmetrization of Dimethyl Cylcohex-4-ene-cis-1,2-dicarboxylate to (1S,2R)-2-(Methoxycarbonyl)cyclohex-4-ene-1-carboxylic Acid

Animesh Goswami and Thomas P. Kissick
pp 483–488
Publication Date (Web): February 16, 2009 (Article)
DOI: 10.1021/op8002954
Figure 1 of 2

Synthesis of the NK1 Receptor Antagonist GW597599. Part 2: Development of a Scalable Route to a Key Chirally Pure Arylpiperazine

Giuseppe Guercio, Angelo Maria Manzo, Michael Goodyear, Sergio Bacchi, Stefano Curti and Stefano Provera
pp 489–493
Publication Date (Web): February 24, 2009 (Article)
DOI: 10.1021/op8002823
Figure 1 of 4

An Investigation of the Transformation of Carbamazepine from Anhydrate to Hydrate Using in Situ FBRM and PVM

Wenju Liu, Hongyuan Wei and Simon Black
pp 494–500
Publication Date (Web): February 19, 2009 (Article)
DOI: 10.1021/op8002773
Figure 1 of 14

Loss Prevention and Waste Minimization with Cascade-Engineered Green Synthesis of Bisphenol-A from Cumene Hydroperoxide and Phenol using Heteropoly Acid-Supported Clay Catalysts

Ganapati D. Yadav and Sanket S. Salgaonkar
pp 501–509
Publication Date (Web): March 5, 2009 (Article)
DOI: 10.1021/op800262u
Figure 1 of 9

Development and Large-Scale Preparation of an Oral TACE Inhibitor

Scott A. Savage, Robert E. Waltermire, Silvio Campagna, Shailendra Bordawekar and Joan Dalla Riva Toma
pp 510–518
Publication Date (Web): March 18, 2009 (Article)
DOI: 10.1021/op800308t
Figure 1 of 2

Process Development of a Potent Bradykinin 1 Antagonist

Karsten Menzel, Fouzia Machrouhi, Matthew Bodenstein, Anthony Alorati, Cameron Cowden, Andrew W. Gibson, Brian Bishop, Norihiro Ikemoto, Todd D. Nelson, Michael H. Kress and Doug E. Frantz
pp 519–524
Publication Date (Web): March 6, 2009 (Article)
DOI: 10.1021/op8003184

Practical, Highly Convergent, Asymmetric Synthesis of a Selective PPARγ Modulator

Peter E. Maligres, Guy R. Humphrey, Jean-Franois Marcoux, Michael C. Hillier, Dalian Zhao, Shane Krska and Edward J. J. Grabowski
pp 525–534
Publication Date (Web): March 9, 2009 (Article)
DOI: 10.1021/op8002882

Development of a Multigram Asymmetric Synthesis of 2-(R)-2-(4,7,10-Tris tert-Butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic Acid, 1-tert-Butyl Ester, (R)-tert-Bu4-DOTAGA

Stuart G. Levy, Vincent Jacques, Kevin Li Zhou, Shirley Kalogeropoulos, Kelly Schumacher, John C. Amedio, Jonathan E. Scherer, Steven R. Witowski, Richard Lombardy and Karsten Koppetsch
pp 535–542
Publication Date (Web): March 20, 2009 (Article)
DOI: 10.1021/op8002932
Figure 1 of 4

Development of a Scaleable Synthesis of a Partial Nicotinic Acid Receptor Agonist

Robert D. Wilson, Ed Cleator, Michael S. Ashwood, Matthew M. Bio, Karel M. J. Brands, Antony J. Davies, Ulf-H. Dolling, Khateeta M. Emerson, Andrew D. Gibb, David Hands, Arlene E. McKeown, Steven F. Oliver, Robert A. Reamer, Faye J. Sheen, Gavin W. Stewart and George X. Zhou
pp 543–547
Publication Date (Web): March 16, 2009 (Article)
DOI: 10.1021/op800290t
Figure 1 of 3

Research and Development of the Catalytic Oxidation of Methylacrylate to 3,3-Dimethoxy Methyl Propionate

Yoshiyuki Tanaka, Jun P. Takahara and Hans E. B. Lempers
pp 548–554
Publication Date (Web): March 18, 2009 (Article)
DOI: 10.1021/op900001p

The Synthesis of a Dopamine D2 Partial Agonist for the Treatment of Schizophrenia

Javier Magano, Alison Acciacca, Anne Akin, Benjamin M. Collman, Brian Conway, Michael Waldo, Michael H. Chen and Kenneth E. Mennen
pp 555–566
Publication Date (Web): March 23, 2009 (Article)
DOI: 10.1021/op800307k
Figure 1 of 3

Manufacture of High-Purity Meloxicam via Its Novel Potassium Salt Monohydrate

Tibor Mezei, Norbert Mesterhzy, Tibor Bak, Mrta Porcs-Makkay, Gyula Simig and Balzs Volk
pp 567–572
Publication Date (Web): March 23, 2009 (Article)
DOI: 10.1021/op900031h
Figure 1 of 3

Pilot Plant Study of Recovery of Lactic Acid from Ethyl Lactate

Prashant P. Barve, Imran Rahman and Bhaskar D. Kulkarni
pp 573–575
Publication Date (Web): March 27, 2009 (Article)
DOI: 10.1021/op800312k
Figure 1 of 2

A Practical, Kilogram-Scale Implementation of the Wolff−Kishner Reduction

Jeffrey T. Kuethe, Karla G. Childers, Zhihui Peng, Michel Journet and Guy R. Humphrey, Thomas Vickery, Donald Bachert and Thientu T. Lam
pp 576–580
Publication Date (Web): April 6, 2009 (Article)
DOI: 10.1021/op9000274

A Simple and Efficient Large-Scale Synthesis of Metal Salts of Medium-Chain Fatty Acids

Boulos Zacharie, Abdallah Ezzitouni, Jean-Simon Duceppe and Christopher Penney
pp 581–583
Publication Date (Web): April 8, 2009 (Article)
DOI: 10.1021/op900038v

Rapid Production of Nitrilase Containing Silica Nanoparticles Offers an Effective and Reusable Biocatalyst for Synthetic Nitrile Hydrolysis

Joshua D. Swartz, Scott A. Miller and David Wright
pp 584–589
Publication Date (Web): April 8, 2009 (Article)
DOI: 10.1021/op9000065
Figure 1 of 4

Combined PAT-Solid State Analytical Approach for the Detection and Study of Sodium Benzoate Hydrate

K. S. Howard, Z. K. Nagy, B. Saha, A. L. Robertson and G. Steele
pp 590–597
Publication Date (Web): April 10, 2009 (Article)
DOI: 10.1021/op800309f
Figure 1 of 13

Utilization of Sequential Palladium-Catalyzed Cross-Coupling Reactions in the Stereospecific Synthesis of Trisubstituted Olefins

Ioannis N. Houpis, Didier Shilds, Ulrike Nettekoven, Anita Schnyder, Erhart Bappert, Koen Weerts, Martine Canters and Wim Vermuelen
pp 598–606
Publication Date (Web): April 22, 2009 (Article)
DOI: 10.1021/op900015g
Figure 1 of 2

Reviews

Continuous Biocatalytic Processes

Nagaraj N. Rao, Stephan Ltz, Kerstin Wrges and Daniel Minr
pp 607–616
Publication Date (Web): March 20, 2009 (Review)
DOI: 10.1021/op800314f
Figure 1 of 9

Communications to the Editor

Enzyme Stabilization by Deposition of Silicone Coatings

Lars O. Wiemann, Petra Weisshaupt, RenNieguth, Oliver Thum and Marion B. Ansorge-Schumacher
pp 617–620
Publication Date (Web): March 18, 2009 (Communication to Editor)
DOI: 10.1021/op9000059
Figure 1 of 6

Preparative Chromatography with Extreme Productivity: HPLC Preparation of an Isomerically Pure Drug Intermediate on Multikilogram Scale

Christopher J. Welch, Derek W. Henderson, David M. Tschaen and Ross A. Miller
pp 621–624
Publication Date (Web): March 25, 2009 (Communication to Editor)
DOI: 10.1021/op900035y
Figure 1 of 5

Practical Asymmetric Hydrogenation of 3-Quinuclidinone Catalyzed by the XylSkewphos/PICA−Ruthenium(II) Complex

Kunihiko Tsutsumi, Takeaki Katayama, Noriyuki Utsumi, Kunihiko Murata, Noriyoshi Arai, Nobuhito Kurono and Takeshi Ohkuma
pp 625–628
Publication Date (Web): April 16, 2009 (Communication to Editor)
DOI: 10.1021/op9000302
Figure 1 of 2

Technical Notes

Hydrogenation of a Pharmaceutical Intermediate by a Continuous Stirred Tank Reactor System

John G. Van Alsten, Matthew L. Jorgensen and David J. am Ende
pp 629–633
Publication Date (Web): February 4, 2009 (Technical Note)
DOI: 10.1021/op800170r
Figure 1 of 9

Application of a Batch Microwave Unit for Scale-Up of Alkoxycarbonylation Reactions Using a Near-Stoichiometric Loading of Carbon Monoxide

Mauro Iannelli, Fabio Bergamelli, Chad M. Kormos, Stefano Paravisi and Nicholas E. Leadbeater
pp 634–637
Publication Date (Web): February 13, 2009 (Technical Note)
DOI: 10.1021/op800296d

Practical One-Pot and Large-Scale Synthesis of N-(tert-Butyloxycarbonyl)-3-pyrroline

Tammana Rajesh, Shaik Abdul Azeez, Erragunta Naresh, Gutta Madhusudhan and Kagga Mukkanti
pp 638–640
Publication Date (Web): February 12, 2009 (Technical Note)
DOI: 10.1021/op8003037
Figure 1 of 3

Practical Synthesis of Roscovitine and CR8

Nassima Oumata, Yoan Ferandin, Laurent Meijer and HervGalons
pp 641–644
Publication Date (Web): February 26, 2009 (Technical Note)
DOI: 10.1021/op800284k

A Convenient One-Step Synthesis of Methyl 2-Benzamidomethyl-3-oxobutanoate

Mingyong Chao, Aiyou Hao and Hui Wang
pp 645–646
Publication Date (Web): February 26, 2009 (Technical Note)
DOI: 10.1021/op800313t

A Simple and Efficient Process for the Preparation of 1,6-Dimethoxynaphthalene

Tianyong Zhang, Qiusheng Yang, Huixian Shi and Lifeng Chi
pp 647–651
Publication Date (Web): March 26, 2009 (Technical Note)
DOI: 10.1021/op800285t
Figure 1 of 3

An Efficient Synthetic Process for Scale-Up Production of 4,5-Diamino-2-(trifluoromethyl)benzonitrile and 5-Bromo-3-(trifluoromethyl)benzene-1,2-diamine

Xun Li, Raymond A. Ng, Yongzheng Zhang, Ronald K. Russell and Zhihua Sui
pp 652–655
Publication Date (Web): April 27, 2009 (Technical Note)
DOI: 10.1021/op9000498
Figure 1 of 2

Book Reviews

Book Review of Guidelines for Hazard Evaluation Procedures

p 656
Publication Date (Web): March 18, 2009 (Book Review)
DOI: 10.1021/op900024b

Book Review of Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions

Trevor Laird
p 656
Publication Date (Web): February 26, 2009 (Book Review)
DOI: 10.1021/op9000252

Book Review of Inherently Safer Chemical Process: A Life Cycle Approach

p 656
Publication Date (Web): March 18, 2009 (Book Review)
DOI: 10.1021/op900026h

Book Review of Pharmaceutical Dosage Forms: Tablets

pp 656–657
Publication Date (Web): March 16, 2009 (Book Review)
DOI: 10.1021/op900036q