title: Nucleophilic aromatic substitution of methacrylamide anion and its application to the synthesis of the anticancer drug bicalutamide.
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.
authors.affiliation: Discovery Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, Princeton, New Jersey 08543, USA. bangchi.chen@bms.com
authors.forename: Bang-Chi
authors.initials: BC
authors.lastname: Chen
authors.forename: Rulin
authors.initials: R
authors.lastname: Zhao
authors.forename: Stacey
authors.initials: S
authors.lastname: Gove
authors.forename: Bei
authors.initials: B
authors.lastname: Wang
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Sundeen
authors.forename: Mark E
authors.initials: ME
authors.lastname: Salvati
authors.forename: Joel C
authors.initials: JC
authors.lastname: Barrish
mesh_terms: 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
chemical_list: D000178:Acrylamides; D000813:Anilides; D000838:Anions; D000970:Antineoplastic Agents; D009570:Nitriles; D014105:Tosyl Compounds; C053541:bicalutamide; C045985:methacrylamide