Synthesis 2002(7): 0850-0852
DOI: 10.1055/s-2002-28508
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Two-step Synthesis of the Anti-cancer Drug (R,S)-Bicalutamide

Kenneth D. James*, Nnochiri N. Ekwuribe
Department of Innovation, Nobex Corporation, 617 Davis Drive; Durham, NC 27713, USA
Fax: +1(919)4749407; e-Mail: kjames@nobexcorp.com; e-Mail: nekwuribe@nobexcorp.com;
Further Information

Publication History

Received 3 February 2002
Publication Date:
14 May 2002 (online)

Abstract

A short, efficient synthesis of the non-steroidal antiandrogen (R,S)-bicalutamide is presented. This new route generates bicalutamide in only two steps with an overall yield of 73%. The key step is a 1,2 addition of a methyl sulfone to a keto-amide.

    References

  • 2a Tucker H. Crook JW. Chesterson GJ. J. Med. Chem.  1988,  31:  954 
  • 2b

    Overall yield was calculated from the reported yields of individual or representative reactions in the synthesis

  • 3 Tucker H. Chesterson GJ. J. Med. Chem.  1988,  31:  885 
  • 4 Ohnmacht CJ. Russell K. Empfield JR. Frank CA. Gibson KH. Mayhugh DR. McLaren FM. Shapiro HS. Brown FJ. Trainor DA. Ceccarelli C. Lin MM. Masek BB. Forst JM. Harris RJ. Hulsizer JM. Lewis JJ. Silverman SM. Smith RW. Warwick PJ. Kau ST. Chun AL. Grant TL. Howe BB. Neilson KL. J. Med. Chem.  1996,  39 :  4592 
  • 5 Fournier JP. Loiseau P. Moreau RC. Narcisse G. Choay P. Eur. J. Med. Chem.  1982,  17:  53 
1

Chem. Abstr., 1986, 101: 54739