Pyridine → HCID 86696298, compound

Participants

Reaction Steps

In a manner similar to the method described in Example 3, 1-chloroethyl carbonochloridate was reacted with 1-methylpiperazine and pyridine in methylene chloride at −78° C. for 3 h to give 1-chloroethyl 4-methylpiperazine-1-carboxylate hydrochloride salt which was reacted with chiral 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid in the presence of cesium carbonate in dimethylformamide overnight to give, after flash chromatography purification (hexane/ethyl acetate, 80/20 to 20/80), 4-methyl-piperazine-1-carboxylic acid 1-(4-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoyloxy)-ethyl ester as a white solid. LCMS (ES+) m/z calcd. for C39H44Cl2F2N5O6 [(M+H)+]: 786, found: 786.

Provenance & Evidence