Development of a synthetic process towards a hepatitis C polymerase inhibitor

Organic Process Research and Development

Volumn 10, Issue 4, 2006, Pages 814-821

  Camp, David ^a   Matthews, Chris F ^a   Neville, Sean T ^a   Rouns, Michael ^a   Scott, Robert W ^a   Truong, Yen ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746884722     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0600761     Document Type: Article

References (11)

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3. (b) Prasad, J. V. N. V.; Boyer, F. E.; Domagala, J. M.; Ellsworth, E. L.; Gajda, C.; Hamilton, H. W.; Hagen, S. E.; Markoski, L. J.; Steinbaugh, B. A.; Tait, B. D.; Humblet, C.; Lunney, E. A.; Pavlovsky, A.; Rubin, J. R.; Ferguson, D.; Graham, N.; Holler, T.; Hupe, D.; Nouhan, C.; Tummino, P. J.; Urumov, A.; Zeikus, E.; Zeikus, G.; Gracheck, S. J.; Saunders, J. M.; VanderRoest, S.; Brodfuehrer, J.; Iyer, K.; Sinz, M.; Gulnik, S. V.; Erickson, J. W. Bioorg. Med. Chem. 1999, 7, 2775-2800.
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5. Compound 15 was synthesized at multiple contract sites using a two-step procedure (addition of cyclopentyl grignard to DMF to produce cyclopentylcarbaldehyde, followed by addition of vinylmagnesium bromide) as outlined in these general literature procedures: Olah, G. A.; Prakash, G. K. S.; Arvanaghi, M. Synthesis, 1984, 3, 228-230;
6. Midland, M. M.; Koops, R. W. J. Org. Chem. 1990, 55, 5058-5065.
7. Brooks, D. W., Lu, L. D. L., Masamune, S. Angew. Chem., Int. Ed. Engl. 1979, 18, 72-74.
8. Allen, C. F. H.; Beilfuss, H. R.; Burness, D. M.; Reynolds, G. A.; Tinker, J. F.; VanAllan, J. A. J. Org. Chem. 1959, 24, 793-6.
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11. The use of isopropyl ether can be hazardous. All fresh solvent, distillates, and waste streams were treated with peroxide-formation inhibitors. Please use with caution.