Phosgene → HCID 178442227, compound

Participants

Reaction Steps

In a manner similar to the method described in Example 4, rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-4-(2,2-dimethyl-propyl)-pyrrolidine-3-carbonitrile (42.3 mg, 0.10 mmol) was reacted with phosgene solution (Aldrich, 20% in toluene, 0.12 mL, 0.12 mmol), in the presence of triethylamine (TEA, 90 mg, 0.90 mmol) in CH2Cl2 (2 mL) followed by reacting with 3-(1H-tetrazol-5-yl)-phenylamine (48.3 mg, 0.30 mmol) at rt for 30 min to give rac-(2S,3S,4S)-2-(3-chloro-2-fluoro-phenyl)-3-(4-chloro-2-fluoro-phenyl)-3-cyano-4-(2,2-dimethyl-propyl)-pyrrolidine-1-carboxylic acid [3-(1H-tetrazol-5-yl)-phenyl]amide (25.3 mg, 41.4%) as a white amorphous. HRMS (ES+) m/z Calcd for C30H27Cl2F2N7O+H [(M+H)+]: 610.1695. found: 610.1695

Provenance & Evidence