Attrition-enhanced deracemization in the synthesis of clopidogrel - A practical application of a new discovery

Organic Process Research and Development

Volumn 13, Issue 6, 2009, Pages 1195-1198

  Van Der Meijden, Maarten W ^a   Leeman, Michel ^a   Gelens, Edith ^a   Noorduin, Wim L ^b   Meekes, Hugo ^b   Van Enckevort, Willem J P ^b   Kaptein, Bernard ^c   Vlieg, Elias ^b   Kellogg, Richard M ^a  

^a Syncom BV   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^c DSM Pharmaceutical Products   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72449145772     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op900243c     Document Type: Article

References (28)

1. 3 from supersaturated solution in contact with solid.
2. (b) Kondepudi, D. K.; Kaufman, R. J.; Singh, N. Science 1990, 250, 975. first demonstrated for an intrinsically chiral compound.
3. (c) Noorduin, W. L.; Izumi, T.; Millemaggi, A.; Leeman, M.; Meekes, H.; van Enckevort, W. J. P.; Kellogg, R. M.; Kaptein, B.; Vlieg, E.; Blackmond, D. G. J. Am. Chem. Soc. 2008, 130, 1158.
4. (a) Cheung, P. S. M.; Gagnon, J.; Surprenant, J.; Tao, Y.; Xu, H.; Cuccia, L. A. Chem. Commun. 2008, 987.
5. (b) Tsogoeva, S.; Mauksch, M. Angew. Chem., Int. Ed. 2009, 48, 590.
6. (c) Viedma, C.; Ortiz, J. E.; De Torres, T.; Izumi, T.; Blackmond, D. B. J. Am. Chem. Soc. 2008, 130, 15274.
7. (d) Kaptein, B.; Noorduin, W. L.; Meekes, H.; van Enckevort, W. J. P.; Kellogg, R. M.; Vlieg, E. Angew. Chem., Int. Ed. 2008, 47, 7226.
8. (a) Coquerel, G. Top. Curr. Chem. 2007, 269, 1-51.
9. (b) Jacques, J.; Collet, A.; Wilen, S. Enantiomers, Racemates and Resolutions; Krieger Pub Co: Malabar, Florida, reprint, 1994; pp 10-20.
10. See for example: (a) Perez-Garcia, L.; Amabilino, D. B. Chem. Soc. Rev. 2007, 36, 941.
11. (b) Leusen, F. Cryst. Growth Des. 2007, 7, 56.
12. Noorduin, W. L.; Kaptein, B.; Meekes, H.; van Enckevort, W. J. P.; Kellogg, R. M.; Vlieg, E. Angew. Chem., Int. Ed. 2009, 48, 4581.
13. MS Global insights, from www.imshealth.com.
14. (a) (Teva Pharmaceutical Industries). U.S. Patent 6,800,759, 2004.
15. (b) (Teva Pharmaceutical Industries). U.S. Patent 6,737,411, 2004.
16. (c) U.S. Patent 4,847,265, 1989.
17. (d) (USV Ltd.). U.S. Patent 6,074,242, 2006.
18. (e) Wang, L.; Shen, J.; Tang, Y.; Chen, Y.; Wang, W.; Cai, Z.; Du, Z. Org. Process Res. Dev. 2007, 11, 487.
19. (a) (USV Ltd.). U.S. Patent 2004073057, 2004.
20. (b) Srinivasa Reddy, B. WO2006003671, 2006.
21. (c) Eswaraiah, S.; Raghupathi Reddy, A.; Goverdhan, G.; Lokeswara Rao, M. U.S. Patent 2007225320, 2007.
22. Galland, A.; Dupray, V.; Berto, B.; Morin-Grognet, S.; Sanselme, M.; Atmani, H.; Coquerel, G. Cryst. Growth Des. 2009, 9, 2713.
23. (a) Leeman, M.; Noorduin, W. L.; Kaptein, B.; Vlieg, E.; Meekes, H.; van Enckevort, W. J. P. Zwaagstra, K.; de Gooijer, J. M.; Boer, K.; Kellogg, R. M. 2009. Manuscripted submitted.
24. 11The cooling procedure described here is technically somewhat easier to carry out on large scale.
25. Noorduin, W. L.; Meekes, H.; van Enckevort, W. J. P.; Millemaggi, A.; Leeman, M.; Kaptein, B.; Kellogg, R. M.; Vlieg, E. Angew. Chem., Int. Ed. 2008, 47, 6445.
26. van Lingen, H. L.; van de Mortel, J. K. W.; Hekking, K. F. W.; van Delft, F. L.; Sonke, T.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2003, 317-324.
27. (Sanofi-Synthelabo). U.S. Patent 6,670,486, 2005.
28. (Patent Hanmi Pharm. Co.). WO2005/87779, 2005.