Trifluoroacetic acid → HCID 90016213, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of chiral 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-benzoic acid 2-((S)-2-tert-butoxycarbonylamino-propionyloxy)-ethyl ester (Example 3, 98.2 mg, 0.118 mmol) in methylene chloride (4 mL) at 0° C. was added trifluoroacetic acid (2 mL) slowly and the mixture was allowed to stir at 0° C. for 1 h. The mixture was concentrated and the residue was taken up in methylene chloride (100 mL), washed successively with aqueous sodium carbonate and water and concentrated. The material was treated with acetonitrile and water and lyophilized to give chiral 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-benzoic acid 2-((S)-2-amino-propionyloxy)-ethyl ester as a white solid (78 mg, 90% yield). MS (ES+) m/z calcd. for C36H39Cl2F2N4O6 [(M+H)+]: 731. found: 731.

Provenance & Evidence