Convergent asymmetric synthesis of two complex TRPV1 antagonists

Organic Process Research and Development

Volumn 15, Issue 5, 2011, Pages 1192-1200

  Butcher, Kenneth J ^a   Denton, Steven M ^a   Field, Stuart E ^a   Gillmore, Adam T ^a   Harbottle, Gareth W ^a   Howard, Roger M ^a   Laity, Daniel A ^a   Ngono, Christian J ^a   Pibworth, Benjamin A ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; BENZYLAMINES; CHIRAL CENTERS; CHIRAL CONTROL; CYCLOPROPANATION; CYCLOPROPYL; ETHYL DIAZOACETATE; SAFETY ASPECTS; SCALE-UP; THERMALLY UNSTABLE;

EID: 80053030488     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200177b     Document Type: Article

References (22)

1. Hutchins, C. W.; Kort, M. E.; Kym, P. R. Biochem. Pharmacol. 2009, 78, 211-216
2. Appendino, G. J. Med. Chem. 2004, 47, 2717-2723
3. Bevan, S.; Boelsteri, J.; Bovermann, G.; Breckenridge, R.; Davies, J. W.; Hughes, G. A.; James, I.; Oberer, L.; Walpole, C. S. J.; Winter, J.; Wrigglesworth, R. J. Med. Chem. 1994, 37, 1942-1954
4. Lee, J. Bioorg. Med. Chem. 2007, 15, 6043
5. Hester, J B. U.S. Patent 5,155,268 A, 1992.
6. Hanazawa, T.; Hirano, M.; Inoue, T.; Nagayama, S.; Nakao, K.; Shishido, Y.; Tanaka, H. International Patent WO 2006/097817 A1, 2006.
7. Hanazawa, T.; Hirano, M.; Inoue, T.; Nagayama, S.; Nakao, K.; Shishido, Y.; Tanaka, H. U.S. Patent 7,622,589 B2, 2009.
8. Ellman, J. A. J. Org. Chem. 1999, 64, 1278
9. Davis, F. A. Tetrahedron 2004, 60, 8003
10. Ellman, J. A.; Herbage, M. A.; Robak, M. T. Chem. Rev. 2010, 110, 3600.
11. Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709
12. Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336
13. Leazer, J. L. J. Org. Chem. 2003, 68, 3695-3698
14. Appleby, I. C. Chem. Ind. 1971, 120
15. Clark, J. D. Thermochim. Acta 2002, 386, 65-72 for Monsanto
16. Nishiyama, H. Bull. Chem. Soc. Jpn. 1995, 68, 1247-1262
17. Gallo, E.; Rose, E. Organometallics 2008, 27, 6143-6151
18. Hanazawa, T.; Hirano, M.; Inoue, T.; Nagayama, S.; Nakao, K.; Shishido, Y.; Tanaka, H. Patent WO 2006/09787
19. Hanazawa, T.; Nagayama, S.; Nakao, K.; Shishido, Y.; Tanaka, H. Patent WO 2007/129188, 2007
20. Cornejo, A. Tetrahedron 2005, 12107-12110
21. Hu, S.; Kline, B. J.; Martinez, C.; Tao, J.; Yazbeck, D. R. Adv. Synth. Catal. 2003, 345, 524-532
22. Montalbetti, C. A. G. N. Tetrahedron 2005, 61, 10827