A simple preparation of a (pyridonyl-1)propargylacetic acid derivative

Organic Process Research and Development

Volumn 10, Issue 4, 2006, Pages 838-840

  Chen, Lijian ^a,b   Dovalsantos, Ellen ^a   Yu, Jian ^a   Lee, Steven ^a,c   O'Neill Slawecki, Stacy ^a,d   Mitchell, Mark ^a   Sakata, Sylvie ^a   Borer, Ben ^a,e  

^a PFIZER INC   (United States)

^b AMGEN INC   (United States)

^c Cortex Pharmaceuticals ^*  (United States)

^d GLAXOSMITHKLINE   (United States)

^e Bioverdant   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746862606     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0600916     Document Type: Article

References (8)

1. For similar HRV 3C protease inhibitors and recent development, see: (a) Dragovich, P. S.; Prins, T. J.; Zhou, R.; Johnson, T. O.; Hua, Y.; Luu, H. T.; Sakata, S. K.; Brown, E. L.; Maldonado, F. C.; Tuntland, T.; Lee, C. A.; Fuhrman, S. A.; Zalman, L. S.; Patick, A. K.; Matthews, D. A.; Wu, E. Y.; Guo, M.; Borer, B. C.; Nayyar, N. K.; Moran, T.; Chen, L.; Rejto, P. A.; Rose, P. W.; Guzman, M. C.; Dovalsantos, E. Z.; Lee, S.; McGee, K.; Mohajeri, M.; Liese, A.; Tao, J.; Kosa, M. B.; Liu, B.; Batugo, M. R.; Gleeson, J.-P. R.; Wu, Z. P.; Liu, J.; Meador, J. W., III; Ferre, R. A. J. Med. Chem. 2003, 46, 4572-4585.
2. (b) Dragovich, P. S.; Prins, T. J.; Zhou, R.; Brown, E. L.; Maldonado, F. C.; Fuhrman, S. A.; Zalman, L. S.; Tuntland, T.; Lee, C. A.; Patick, A. K.; Matthews, D. A.; Hendrickson, T. F.; Kosa, M. B.; Liu, B.; Batugo, M. R.; Gleeson, J.-P. R.; Sakata, S. K.; Chen, L.; Guzman, M. C.; Meador, J. W., III; Ferre, R. A.; Worland, S. T. J. Med. Chem. 2002, 45, 1607-1623.
3. (c) Dragovich P. S. Expert Opin. Ther. Pat. 2001, 11, 177-184.
4. Martinez, C. A.; Yazbeck, D. R.; Tao, J. Tetrahedron 2004, 60, 759-764.
5. Krapcho, A. P.; Weimaster, J. F.; Eldridge, J. M.; Jahngen, E. G. E.; Lovey, A. J.; Stephens, W. P. J. Org. Chem. 1978, 43, 138-147.
6. An unknown impurity with a molecular weight of about twice that of compound 6 was detected in an appreciable amount in concentrated reaction mixture.
7. 4, pH 4.0 (60%) and acetonitrile (40%), and a total run time of 35 min.
8. The undesired enantiomerically enriched (R)-1 was obtained in > 95% recovery and ∼50% ee through acid-base extractive workup.