Development of a novel Pd-catalyzed N-acyl vinylogous carbamate synthesis for the key intermediate of ICE inhibitor VX-765

Organic Letters

Volumn 10, Issue 2, 2008, Pages 185-188

  Tanoury, Gerald J ^a   Chen, Minzhang ^a   Dong, Yong ^a   Forslund, Raymond E ^a   Magdziak, Derek ^a  

^a VERTEX PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 ((1 (4 AMINO 3 CHLOROPHENYL)METHANOYL)AMINO) 3,3 DIMETHYLBUTANOYL)PYRROLIDINE 2 CARBOXYLIC ACID; 1-(2-((1-(4-AMINO-3-CHLOROPHENYL)METHANOYL)AMINO)-3,3-DIMETHYLBUTANOYL)PYRROLIDINE-2-CARBOXYLIC ACID; 4 AMINOBENZOIC ACID; ACRYLAMIDE; BROMINATED HYDROCARBON; CARBAMIC ACID DERIVATIVE; DIPEPTIDE; DRUG DERIVATIVE; INTERLEUKIN 1BETA CONVERTING ENZYME; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

4-AMINOBENZOIC ACID; ACRYLAMIDE; CARBAMATES; CASPASE 1; CATALYSIS; DIPEPTIDES; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 38749130873     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702532h     Document Type: Article

References (30)

1. (a) Wood, D. D.; Ihrie, E. J.; Dinarello, C. A.; Cohen, P. L. Arthritis Rheum. 1983, 26, 975.
2. (b) Pettipher, E. J.; Higgs, G. A.; Henderson, B. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8749.
3. (c) Bataille, R.; Chappard, D.; Bernard, K. Int. J. Clin. Lab. Res. 1992, 21, 283.
4. (d) Vidal-Vanaclocha, F.; Amezaga, C.; Asumendi, A.; Kaplanski, G.; Dinarello, C. A. Cancer Res. 1994, 54, 2667.
5. (a) Sleath, P. R.; Hendrickson, R. C.; Kronheim, S. R.; March, C. J.; Black, R. A. J. Biol. Chem. 1990, 265, 14526.
6. (b) Howard, A. D.; Kostura, J. R.; Thornberry, N.; Ding, G. J.; Limjuco, G.; Weidner, J.; Salley, J. P.; Hogquist, K. A.; Chaplin, D. D.; Mumford, R. A. J. Immunol. 1991, 147, 2964.
7. (c) Black, R. A.; Kronheim, S. R.; Sleath, P. R. FEBS Lett. 1989, 386.
8. (d) Kostura, M. J.; Tocci, M. J.; Limjuco, G.; Chin, J.; Cameron, P.; Hillman, A. G.; Chartrain, N. A.; Schmidt, J. A. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5227.
9. (e) Steller, H. Science 1995, 267, 1445.
10. For leading references to VX-765, see: (a) Wannamaker, W.; Davies, R.; Namchuk, M.; Pollard, J.; Ford, P.; Ku, G.; Decker, C.; Charifson, P.; Weber, P.; Germann, U. A.; Keisuke, K.; Randle, J. C. R. J. Pharmacol. Exp. Ther. 2007, 32, 509.
11. (b) Stake, J. H.; Beaumont, K.; Larsen, P. D.; Straley, K. S.; Henkel, G. W.; Randle, J. C. R.; Hoffman, H. M. J. Immunol. 2005, 175, 2630.
12. (c) Ravizza, T.; Lucas, S.-B.; Silvia, B.; Bernardino, L.; Ku, G.; Noe, F.; Malva, J.; Randle, J. C. R.; Allan, S.; Vezzani, A. Epilepsia 2006, 47, 1160.
13. For leading references to caspase inhibitors, see: (d) Cornelis, S.; Kerrse, K.; Festiens, N.; Lamkanfi, M.; Vandenabeele, P. Curr. Pharm. Des. 2007, 13, 367.
14. (e) Linton, S. D. Curr. Top. Med. Chem. 2005, 5, 1697.
15. (a) Han, C.; Shen, R.; Su, S.; Porco, J. A., Jr. Org. Lett. 2004, 6, 27.
16. Also see: (b) Buckler, R. T.; Hartzler, H. E. J. Med. Chem. 1975, 18, 509.
17. (c) Boger, D. L.; Wysocki, R. J., Jr. J. Org. Chem. 1989, 54, 714.
18. (d) Hosokawa, T.; Takano, M.; Kuroki, Y.; Murahashi, S. I. Tetrahedron Lett. 1992, 33, 6643.
19. (e) Suh, E. M.; Kishi, Y. J. Am. Chem. Soc. 1994, 116, 11205.
20. For related Cu-catalyzed coupling of amides, see: (a) Jiang, L.; Job, G. E.; Kalpars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
21. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
22. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
23. (d) Shen, R.; Porco, J. A. Org. Lett. 2000, 2, 1333.
24. (e) Guo, X.; Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Adv. Synth. Catal. 2006, 348, 2197.
25. (f) Lee, J. M.; Ahn, D.-S.; Jung, D. Y.; Lee, J.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006, 128, 12954.
26. Also see: (a) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809-1812.
27. (b) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035-2038.
28. (c) Willis, M. C.; Brace, G. N.; Holmes, I. P. Synthesis 2005, 3229-3234.
29. (d) Lee, J. M.; Ahn, D.-S.; Jung, D. Y.; Lee, J. G.; Do, Y.; Kim, S. K.; Chang, S. J. Am. Chem. Soc. 2006, 128, 12954.
30. (e) Villa, M. V. J.; Targett, S. M.; Barnes, J. C.; Whittingham, W. G.; Marquez, R. Org. Lett. 2007, 9, 1631.