Ethanol → (2S,4R)-2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)pyrrolidinium chloride

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of ethanol at 0° C., was added acetyl chloride (1.77 kg). The resulting solution was aged for 30 min. (2S,4R)-tert-Butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)pyrrolidine-1-carboxylate (2.34 kg) was then added as a solution in EtOAc (8.36 kg) to the acidic ethanol slurry solution at 10° C. The reaction was allowed to proceed for 1 h at 10° C., warmed to 15° C., held at that temperature for 1 h and then warmed to 20° C. After 18 h, EtOAc (8.35 kg) was added to the reactor and the resulting slurry was filtered. The cake was rinsed with EtOAc (8.35 kg) that had been cooled to 0° C. The title compound was placed in a vacuum oven, at 40° C., to remove residual solvent (2.1 kg, 100% yield).

Provenance & Evidence