Table of Contents

November 20, 2009
Volume 13, Issue 6
Pages 1037-1432

 

Polymorphism and Crystallization
Editorial

Some Thoughts on Generic API Manufacture

Trevor Laird
p 1037
Publication Date (Web): October 30, 2009 (Editorial)
DOI: 10.1021/op9002664

Highlights from the Literature

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

Mark McLaughlin, Silvina Garca Rubio, Ulf Tilstam, Trevor Laird, Andrei Zlota
pp 1038–1045
Publication Date (Web): November 3, 2009 (Highlights from the Literature)
DOI: 10.1021/op900270h

Highlights from the Patents

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

Keith Turner
pp 1046–1058
Publication Date (Web): October 28, 2009 (Highlights From Patents)
DOI: 10.1021/op900261t

Concept Article

An Efficient Laboratory Automation Concept for Process Chemistry

Christian Bernlind and Csaba Urbaniczky
pp 1059–1067
Publication Date (Web): September 23, 2009 (Concept Article)
DOI: 10.1021/op900154c
Figure 1 of 7

Full Papers

Removal of Heavy Metals from Organic Reaction Mixtures: Preparation and Application of Functionalized Resins

Damien Barbaras, Jrg Brozio, Ib Johannsen and Thomas Allmendinger
pp 1068–1079
Publication Date (Web): October 20, 2009 (Article)
DOI: 10.1021/op900102a
Figure 1 of 3

Evaluation and Establishment of a Cleaning Protocol for the Production of Vanisal Sodium and Aspirin Using a Continuous Oscillatory Baffled Reactor

Caldeira Ricardo and Ni Xiongwei
pp 1080–1087
Publication Date (Web): October 6, 2009 (Article)
DOI: 10.1021/op900120h
Figure 1 of 12

Pilot-Plant Preparation of an αvβ3 Integrin Antagonist. Part 3. Process Research and Development of a Diisopropylcarbodiimide and Catalytic 1-Hydroxybenzotriazole Peptide Coupling

Jerry D. Clark, D. Keith Anderson, David V. Banaszak, Derek B. Brown, Ann M. Czyzewski, Albert D. Edeny, Puneh S. Forouzi, Donald J. Gallagher, V. H. Iskos, H. Peter Kleine, Carl M. Knable, Melissa K. Lantz, Mark A. Lapack, Christine M. V. Moore, Frank W. Muellner, James B. Murphy, Carlos A. Orihuela, Mark A. Pietz, Thomas E. Rogers, Peter G. Ruminski, Harish K. Santhanam, Tobin C. Schilke, Ajit S. Shah, Ahmad Y. Sheikh, Gerald A. Weisenburger and Bruce E. Wise
pp 1088–1093
Publication Date (Web): September 4, 2009 (Article)
DOI: 10.1021/op900173f
Figure 1 of 4

A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction

Michael J. Girgis, Jessica K. Liang, Zhengming Du, Joel Slade and Kapa Prasad
pp 1094–1099
Publication Date (Web): September 23, 2009 (Article)
DOI: 10.1021/op900192m
Figure 1 of 7

Synthesis of the NK1 Receptor Antagonist GW597599. Part 3: Development of a Scalable Route to a Key Chirally Pure Arylpiperazine Urea, A Happy End

Giuseppe Guercio, Sergio Bacchi, Alcide Perboni, Corinne Leroi, Francesco Tinazzi, Ilaria Bientinesi, Marie Hourdin, Michael Goodyear, Stefano Curti, Stefano Provera and Zadeo Cimarosti
pp 1100–1110
Publication Date (Web): October 2, 2009 (Article)
DOI: 10.1021/op9002032
Figure 1 of 7

An Efficient Synthesis of a Cyclic Ether Key Intermediate for 9-Membered Masked Enediyne Using an Automated Synthesizer

Yoshikazu Tanaka, Shinichiro Fuse, Hiroshi Tanaka, Takayuki Doi and Takashi Takahashi
pp 1111–1121
Publication Date (Web): November 2, 2009 (Article)
DOI: 10.1021/op9002455
Figure 1 of 3

Scalable Process for the Premix of Esomeprazole

Lekkala Amarnath Reddy, Golla China Malakondaiah, Alieti Sanjay Reddy, Boluguddu Vijaya Bhaskar, Vurimidi Himabindu, Apurba Bhattacharya and Rakeshwar Bandichhor
pp 1122–1124
Publication Date (Web): September 25, 2009 (Article)
DOI: 10.1021/op9001406
Figure 1 of 3

Development of Manufacturing Processes for a New Family of 2,6-Dihaloaryl 1,2,4-Triazole Insecticides

John W. Hull, Jr., Duane R. Romer, Timothy J. Adaway and David E. Podhorez
pp 1125–1129
Publication Date (Web): November 2, 2009 (Article)
DOI: 10.1021/op9001577

Process Development and Scale Up of a Glycine Antagonist

Adam Banks, Gary F. Breen, Darren Caine, John S. Carey, Christopher Drake, Michael A. Forth, Asa Gladwin, Simone Guelfi, Jerome F. Hayes, Paolo Maragni, David O. Morgan, Paul Oxley, Alcide Perboni, Matthew E. Popkin, Fiona Rawlinson and Guillaume Roux
pp 1130–1140
Publication Date (Web): September 23, 2009 (Article)
DOI: 10.1021/op9001824
Figure 1 of 7

Short and Efficient Process for the Synthesis of trans-4-Aminocyclohexanecarboxylic Acid Derivatives

Pankaj S. Patil, Ulhas S. Mahajan, Swapnil P. Sonawane and Mukund K. Gurjar
pp 1141–1144
Publication Date (Web): October 14, 2009 (Article)
DOI: 10.1021/op900195w

Development of a Scalable Synthesis of Dipeptidyl Peptidase-4 Inhibitor ABT-279

Todd S. McDermott, Lakshmi Bhagavatula, Thomas B. Borchardt, Kenneth M. Engstrom, Jorge Gandarilla, Brian J. Kotecki, Albert W. Kruger, Michael J. Rozema, Ahmad Y. Sheikh, Seble H. Wagaw and Steven J. Wittenberger
pp 1145–1155
Publication Date (Web): October 15, 2009 (Article)
DOI: 10.1021/op900197r
Figure 1 of 3

An Efficient Kilogram-Scale Synthesis of N,N′-Bis(4,6-disubstituted 1,3,5-triazin-2-yl)-4-aminophenetylamine

Jean-Simon Duceppe, Valrie Perron, Jose Cloutier, Christopher Penney and Boulos Zacharie
pp 1156–1160
Publication Date (Web): October 1, 2009 (Article)
DOI: 10.1021/op900202b

Practical Enantioselective Synthesis of a 3-Aryl-3-trifluoromethyl-2-aminopropanol Derivative

Asaf Alimardanov, Antonia Nikitenko, Terrence J. Connolly, Gregg Feigelson, Anita W. Chan, Zhixian Ding, Mousumi Ghosh, Xinxu Shi, Jianxin Ren, Eric Hansen, Roger Farr, Michael MacEwan, Sam Tadayon, Dane M. Springer, Anthony F. Kreft, Douglas M. Ho and John R. Potoski
pp 1161–1168
Publication Date (Web): October 27, 2009 (Article)
DOI: 10.1021/op900216v
Figure 1 of 4

Preparation of Saxagliptin, a Novel DPP-IV Inhibitor

Scott A. Savage, Gregory S. Jones, Sergei Kolotuchin, Shelly Ann Ramrattan, Truc Vu and Robert E. Waltermire
pp 1169–1176
Publication Date (Web): October 16, 2009 (Article)
DOI: 10.1021/op900226j
Figure 1 of 3

Development of a Scalable Synthetic Process for DG-051B, A First-in-Class Inhibitior of LTA4H

Livia A. Enache, Isaac Kennedy, David W. Sullins, Wei Chen, Dragan Ristic, Glenn L. Stahl, Sergey Dzekhtser, Robert A. Erickson, Changren Yan, Frank W. Muellner, Michael D. Krohn, Jennifer Winger, Vincent Sandanayaka, Jasbir Singh, David E. Zembower and Alex S. Kiselyov
pp 1177–1184
Publication Date (Web): November 2, 2009 (Article)
DOI: 10.1021/op900231j
Figure 1 of 2

New and Improved Manufacturing Process for Valsartan

Senthil Kumar .N, Shankar B. Reddy, Brajesh Kumar Sinha, Kagga Mukkanti and Ramesh Dandala
pp 1185–1189
Publication Date (Web): October 13, 2009 (Article)
DOI: 10.1021/op9000912

Communications to the Editor

An Improved Process for Pioglitazone and Its Pharmaceutically Acceptable Salt

Lokeswara Rao Madivada, Raghupathi Reddy Anumala, Goverdhan Gilla, Sampath Alla, Kavitha Charagondla, Mukkanti Kagga, Apurba Bhattacharya and Rakeshwar Bandichhor
pp 1190–1194
Publication Date (Web): September 29, 2009 (Communication to Editor)
DOI: 10.1021/op900131m
Figure 1 of 2

Attrition-Enhanced Deracemization in the Synthesis of Clopidogrel - A Practical Application of a New Discovery

Maarten W. van der Meijden, Michel Leeman, Edith Gelens, Wim L. Noorduin, Hugo Meekes, Willem J. P. van Enckevort, Bernard Kaptein, Elias Vlieg and Richard M. Kellogg
pp 1195–1198
Publication Date (Web): November 4, 2009 (Communication to Editor)
DOI: 10.1021/op900243c

Green N-Methylation of Electron Deficient Pyrroles with Dimethylcarbonate

Michael L. Laurila, Nicholas A. Magnus and Michael A. Staszak
pp 1199–1201
Publication Date (Web): October 26, 2009 (Communication to Editor)
DOI: 10.1021/op900256t

A Continuously Operated Bimembrane Reactor Process for the Biocatalytic Production of (2R,5R)-Hexanediol

Kirsten Schroer and Stephan Ltz
pp 1202–1205
Publication Date (Web): October 16, 2009 (Communication to Editor)
DOI: 10.1021/op9001643
Figure 1 of 5

Technical Notes

An Improved Synthetic Route for Preparative Process of Vardenafil

Yongjun Mao, Guanghui Tian, Zheng Liu, Jingkang Shen and Jingshan Shen
pp 1206–1208
Publication Date (Web): November 2, 2009 (Technical Note)
DOI: 10.1021/op900235p
Figure 1 of 2

Technology Reports

Online Reaction Monitoring and Evaluation of Kinetic Parameters for Dilute Reactions Using Refractive Index Measurements

Martin Tjahjono, Effendi Widjaja and Marc Garland
pp 1209–1213
Publication Date (Web): September 8, 2009 (Technology Report)
DOI: 10.1021/op9001388
Figure 1 of 5

Editorial

Special Polymorphism and Crystallisation Feature Section

Trevor Laird
p 1214
Publication Date (Web): November 3, 2009 (Editorial)
DOI: 10.1021/op900268n

Reviews

Particle Engineering Strategies via Crystallization for Pulmonary Drug Delivery

Doaa M. Ragab and Sohrab Rohani
pp 1215–1223
Publication Date (Web): June 19, 2009 (Review)
DOI: 10.1021/op900013a
Figure 1 of 3

Lecture Transcripts

Turning DSC Charts of Polymorphs into Phase Diagrams: A Tutorial Paper

Terence L. Threlfall
pp 1224–1230
Publication Date (Web): November 4, 2009 (Lecture Transcript)
DOI: 10.1021/op900158a
Figure 1 of 12

Why Do Organic Compounds Crystallise Well or Badly or Ever so Slowly? Why Is Crystallisation Nevertheless Such a Good Purification Technique?

Michael B. Hursthouse, L. Susanne Huth and Terence L. Threlfall
pp 1231–1240
Publication Date (Web): November 20, 2009 (Lecture Transcript)
DOI: 10.1021/op900169b
Figure 1 of 11

Reviews

Polymorphism in Processes of Crystallization in Solution: A Practical Review

Denis Mangin, Francois Puel and Stephane Veesler
pp 1241–1253
Publication Date (Web): October 1, 2009 (Review)
DOI: 10.1021/op900168f
Figure 1 of 7

Full Papers

Endoscopy-Based in Situ Bulk Video Imaging of Batch Crystallization Processes

Levente L. Simon, Zoltan K. Nagy and Konrad Hungerbuhler
pp 1254–1261
Publication Date (Web): May 11, 2009 (Article)
DOI: 10.1021/op900019b
Figure 1 of 15

Polymorphic Crystallization and Transformation of the Anti-Viral/HIV Drug Stavudine

Jie Lu and Sohrab Rohani
pp 1262–1268
Publication Date (Web): June 5, 2009 (Article)
DOI: 10.1021/op900004c
Figure 1 of 13

Preparation and Characterization of Theophylline−Nicotinamide Cocrystal

Jie Lu and Sohrab Rohani
pp 1269–1275
Publication Date (Web): May 28, 2009 (Article)
DOI: 10.1021/op900047r
Figure 1 of 12

A Novel Crystallization Methodology To Ensure Isolation of the Most Stable Crystal Form

Aaron Cote, George Zhou and Mary Stanik
pp 1276–1283
Publication Date (Web): October 1, 2009 (Article)
DOI: 10.1021/op900095n
Figure 1 of 12

Crystallisation from Water-in-Oil Emulsions As a Route to Spherical Particulates: Glycine and the Hydrochloride Salts of Glutamic Acid and Ephedrine

K. Chadwick, R. J. Davey and R. Mughal, I. Marziano
pp 1284–1290
Publication Date (Web): August 11, 2009 (Article)
DOI: 10.1021/op900123n
Figure 1 of 9

Solvent Effects on the Crystallization and Preferential Nucleation of Carbamazepine Anhydrous Polymorphs: A Molecular Recognition Perspective

Ron C. Kelly and Nar Rodrguez-Hornedo
pp 1291–1300
Publication Date (Web): October 7, 2009 (Article)
DOI: 10.1021/op900133z
Figure 1 of 16

The Effect of Temperature and Solvent Composition on Transformation of β- to α-Glycine As Monitored in Situ by FBRM and PVM

Leping Dang, Huaiyu Yang, Simon Black and Hongyuan Wei
pp 1301–1306
Publication Date (Web): August 28, 2009 (Article)
DOI: 10.1021/op900134w
Figure 1 of 15

A Practical Solid Form Screen Approach To Identify a Pharmaceutical Glutaric Acid Cocrystal for Development

Zhibin Li, Bing-Shiou Yang, Mo Jiang, Magnus Eriksson, Earl Spinelli, Nathan Yee and Chris Senanayake
pp 1307–1314
Publication Date (Web): October 6, 2009 (Article)
DOI: 10.1021/op900137j
Figure 1 of 6

A Practical Approach for Using Solubility to Design Cooling Crystallisations

Frans L. Muller, Mark Fielding and Simon Black
pp 1315–1321
Publication Date (Web): October 30, 2009 (Article)
DOI: 10.1021/op9001438
Figure 1 of 8

The Solubility of Beclomethasone-17,21-dipropionate in Selected Organic Solvents: Experimental Measurement and Thermodynamic Modeling

Yousef Bakhbakhi, Paul Charpentier and Sohrab Rohani
pp 1322–1326
Publication Date (Web): September 3, 2009 (Article)
DOI: 10.1021/op900142j
Figure 1 of 3

The Challenges of Developing an API Crystallization Process for a Complex Polymorphic and Highly Solvating System. Part I

Brian P. Chekal, Anthony M. Campeta, Yuriy A. Abramov, Neil Feeder, Paul P. Glynn, Robert W. McLaughlin, Paul A. Meenan and Robert A. Singer
pp 1327–1337
Publication Date (Web): November 4, 2009 (Article)
DOI: 10.1021/op9001559
Figure 1 of 10

A Rapid Method for Screening Crystallization Conditions and Phases of an Active Pharmaceutical Ingredient

Thibaud Detoisien, Maxime Forite, Pascal Taulelle, Jol Teston, Didier Colson, Jean Paul Klein and Stphane Veesler
pp 1338–1342
Publication Date (Web): September 29, 2009 (Article)
DOI: 10.1021/op9001593
Figure 1 of 8

Seeded Batch Cooling Crystallization with Temperature Cycling for the Control of Size Uniformity and Polymorphic Purity of Sulfathiazole Crystals

Mohd R. Abu Bakar, Zoltan K. Nagy and Chris D. Rielly
pp 1343–1356
Publication Date (Web): November 3, 2009 (Article)
DOI: 10.1021/op900174b
Figure 1 of 18

Continuous Crystallization of Pharmaceuticals Using a Continuous Oscillatory Baffled Crystallizer

Simon Lawton, Gerry Steele and Phil Shering, Lihua Zhao and Ian Laird, Xiong-Wei Ni
pp 1357–1363
Publication Date (Web): October 27, 2009 (Article)
DOI: 10.1021/op900237x
Figure 1 of 8

Crystallization Behavior of Polymorphic Mixtures of MPPO

Yoshitaka Nakata, Youko Kiyosawa, Kooji Kagara and Masakuni Matsuoka
pp 1364–1369
Publication Date (Web): October 28, 2009 (Article)
DOI: 10.1021/op900220m
Figure 1 of 12

A Low-Waste Process To Sertraline By Diastereomeric Crystal Resolution and Waste Isomer Racemisation

A. John Blacker, Stuart Brown, Blandine Clique, Brian Gourlay, Catherine E. Headley, Stephen Ingham, Dougal Ritson, Thomas Screen, Matthew J. Stirling, David Taylor and Gary Thompson
pp 1370–1378
Publication Date (Web): July 17, 2009 (Article)
DOI: 10.1021/op900112f
Figure 1 of 5

The Resolution of 2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-Oxide (Phencyphos) by Preferential Crystallization

Michel Leeman, Florian Querniard, T. R. Vries, Bernard Kaptein and Richard M. Kellogg
pp 1379–1381
Publication Date (Web): August 19, 2009 (Article)
DOI: 10.1021/op900171k
Figure 1 of 5

A Novel Chiral Resolving Reagent, Bis((S)-Mandelic acid)-3-nitrophthalate, for Amlodipine Racemate Resolution: Scalable Synthesis and Resolution Process

Hong Woo Lee, Sung Jae Shin, Hosung Yu, Sung Kwon Kang and Choong Leol Yoo
pp 1382–1386
Publication Date (Web): October 2, 2009 (Article)
DOI: 10.1021/op900070c
Figure 1 of 3

Editorial

Special Safety Feature Section

Trevor Laird
p 1387
Publication Date (Web): November 3, 2009 (Editorial)
DOI: 10.1021/op900267d

Highlights from the Literature

Safety Notables: Information from the Literature

Richard W. Barnhart, David J. Dale, Michael D. Ironside, Paul F. Vogt
pp 1388–1394
Publication Date (Web): November 20, 2009 (Highlights from the Literature)
DOI: 10.1021/op900254g

Concept Article

Practical Segregation of Incompatible Reagents in the Organic Chemistry Laboratory

John J. M. Wiener and Cheryl A. Grice
pp 1395–1400
Publication Date (Web): June 8, 2009 (Concept Article)
DOI: 10.1021/op900094d
Figure 1 of 10

Full Papers

A Convenient and Stable Synthon for Ethyl Azide and Its Evaluation in a [3 + 2]-Cycloaddition Reaction under Continuous-Flow Conditions

Rob Tinder, Roger Farr, Richard Heid, Ralph Zhao, Randy S. Rarig, Jr. and Thomas Storz
pp 1401–1406
Publication Date (Web): May 28, 2009 (Article)
DOI: 10.1021/op900078t
Figure 1 of 6

Efficient Synthesis of 1,4-Diaryl-5-methyl-1,2,3-triazole, A Potential mGluR1 Antagonist, and the Risk Assessment Study of Arylazides

Takayuki Tsuritani, Hiroo Mizuno, Nobuaki Nonoyama, Satoshi Kii, Atsushi Akao, Kimihiko Sato, Nobuyoshi Yasuda and Toshiaki Mase
pp 1407–1412
Publication Date (Web): May 12, 2009 (Article)
DOI: 10.1021/op900062p
Figure 1 of 5

Practical Diastereoselective Synthesis and Scale-up Study of (+)-2-((1R,2R,3R,5S)-2-Amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)ethanol: A Key Intermediate of the Novel Prostaglandin D2 Receptor Antagonist S-5751

Takemasa Hida, Susumu Mitsumori, Tsunetoshi Honma, Yoshiharu Hiramatsu, Hiroshi Hashizume, Tetsuo Okada, Makoto Kakinuma, Kyozo Kawata, Katsuo Oda, Aiko Hasegawa, Toshiaki Masui and Hideo Nogusa
pp 1413–1418
Publication Date (Web): July 2, 2009 (Article)
DOI: 10.1021/op9001092
Figure 1 of 9

The Discovery and Development of a Safe, Practical Synthesis of ABT-869

Albert W. Kruger, Michael J. Rozema, Alexander Chu-Kung, Jorge Gandarilla, Anthony R. Haight, Brian J. Kotecki, Steven M. Richter, Albert M. Schwartz and Zhe Wang
pp 1419–1425
Publication Date (Web): October 28, 2009 (Article)
DOI: 10.1021/op900208y
Figure 1 of 2

Technical Notes

Formation of 2-Trifluoromethylphenyl Grignard Reagent via Magnesium−Halogen Exchange: Process Safety Evaluation and Concentration Effect

Wenjun Tang, Max Sarvestani, Xudong Wei, Laurence J. Nummy, Nitinchandra Patel, Bikshandarkoil Narayanan, Denis Byrne, Heewon Lee, Nathan K. Yee and Chris H. Senanayake
pp 1426–1430
Publication Date (Web): June 25, 2009 (Technical Note)
DOI: 10.1021/op900040y
Figure 1 of 3

Book Reviews

Book Review of Green Catalysis

Trevor Laird
p 1431
Publication Date (Web): October 30, 2009 (Book Review)
DOI: 10.1021/op900273n

Book Review of Flash Chemistry: Fast Organic Synthesis in Microsystems

Trevor Laird
p 1432
Publication Date (Web): October 30, 2009 (Book Review)
DOI: 10.1021/op900275q

Book Review of Catalysis of Organic Reactions

Trevor Laird
p 1432
Publication Date (Web): November 2, 2009 (Book Review)
DOI: 10.1021/op900276m