Dimethyl Sulfide → HCID 53357741, compound

Participants

Reaction Steps

To a solution of ethyl 5-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)pyrazine-2-carboxylate (27.6 mg, 0.0448 mmol) in dichloromethane (2 ml) were added DIMETHYL SULFIDE (846 mg, 0.0136 mmol) and ALUMINUM BROMIDE (64.5 mg, 0.242 mmol). The mixture was stirred under argon for 5 hrs. The reaction mixture was diluted with acetonitrile (2 ml), EtOAc (10 ml) and water (10 ml) and stirred for several minutes. After more ethyl acetate (50 ml) was added, the organic layer was separated and washed with saturated ammonium chloride (10 ml), water (10 ml) and sat. sodium chloride (10 ml). The organic layers were dried over Na2SO4 and concentrated and purified by silica gel chromatography with methanol and dichloromethane to give chiral 5-{[(2R,3S,4R,5S)-4-(4-Chloro-2-fluoro-phenyl)-3-(3-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-pyrazine-2-carboxylic acid as an off-white lyophilized solid (19.7 mg, 74%). MS (ES+) m/z Calcd: [(M+H)+]: 588.13. found: 588.0

Provenance & Evidence