Methanol → HCID 72548159, compound

Participants

Reaction Steps

In a 4 dram vial, 2-((2,2-dimethyl-1,3-dioxolan-4-yl)methylamino)-2-oxoethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate (Example 67, 67 mg, 85.1 μmol) was combined with methanol (1 mL), methylene chloride (0.5 mL) and water (2 drops) to give a colorless solution. Trifluoroacetic acid (19.4 mg, 13.1 μL, 170 μmol) was added. The reaction mixture was stirred at room temperature for 5 h then concentrated. The residue was reconstituted with methylene chloride (100 mL). It was washed with saturated aqueous sodium carbonate solution, then brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude residuw was purified by flash chromatography (23 g SUPELCO spherical silica gel column, eluted with methanol in ethyl acetate) to give 4-{[(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}-3-methoxy-benzoic acid (2,3-dihydroxy-propylcarbamoyl)-methyl ester (23 mg, 36% yield). LCMS (ES+) m/z calcd. for C36H39Cl2F2N4O7 [(M+H)+]: 747. found: 747.

Provenance & Evidence