Cesium carbonate → HCID 71738055, compound

Participants

Reaction Steps

To a solution of 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoic acid (215 mg, 0.349 mmol) in dimethylformamide (22 mL) was added cesium carbonate (2.15 g, 6.6 mmol). After stirring for 10 min, a solution of the freshly made benzyl 2-((1-chloroethoxy)carbonylamino)acetate (2.77 g crude, ˜5.55 mmol) in dimethylformamide (5 mL) was added. The reaction mixture was allowed to stir at room temperature overnight. This reaction mixture was taken up in ethyl acetate, washed with water, brine and concentrated to dryness. The crude material was purified by flash chromatography (hexane/ethyl acetate, 90/10 to 10/90) to give 1-(2-(benzyloxy)-2-oxoethylcarbamoyloxy)ethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate as a white solid (191 mg, 64% yield). LCMS (ES+) m/z calcd. for C43H43Cl2F2N4O8 [(M+H)+]: 851, found: 851.

Provenance & Evidence