Nucleophilic aromatic substitution of methacrylamide anion and its application to the synthesis of the anticancer drug bicalutamide

J Org Chem. 2003 Dec 26;68(26):10181-2. doi: 10.1021/jo035377c.

Abstract

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.

MeSH terms

  • Acrylamides / chemistry*
  • Anilides / chemical synthesis*
  • Anilides / chemistry
  • Anions / chemistry
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Nitriles
  • Stereoisomerism
  • Tosyl Compounds

Substances

  • Acrylamides
  • Anilides
  • Anions
  • Antineoplastic Agents
  • Nitriles
  • Tosyl Compounds
  • bicalutamide
  • methacrylamide