Nucleophilic aromatic substitution of methacrylamide anion and its application to the synthesis of the anticancer drug bicalutamide.
The anticancer drug (R,S)-biscaltamide was prepared in three steps in >90% overall yield. A key step in the new synthesis involved a new nucleophilic aromatic substitution reaction of methacrylamide anion.
Chen
Bang-Chi
BC
Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, New Jersey 08543, USA. bangchi.chen@bms.com
Zhao
Rulin
R
Gove
Stacey
S
Wang
Bei
B
Sundeen
Joseph E
JE
Salvati
Mark E
ME
Barrish
Joel C
JC
D000178:Acrylamides / Q000737:chemistry*; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D000838:Anions / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009570:Nitriles; D013237:Stereoisomerism; D014105:Tosyl Compounds
D000178:Acrylamides; D000813:Anilides; D000838:Anions; D000970:Antineoplastic Agents; D009570:Nitriles; D014105:Tosyl Compounds; C053541:bicalutamide; C045985:methacrylamide