Hydrogen Peroxide → Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-benzyloxycarbonylamino-2-cyanosuccinic acid diethyl ester (15.4 g) in dichloromethane (50 ml) was cooled to ice-bath temperature, and then 30% hydrogen peroxide (21 ml), tetrabutylammonium hydrogen sulfate (3.0 g) and 20% aqueous sodium hydroxide solution (16.6 ml) were added in turn. The resulting mixture was stirred under ice cooling for 30 minutes and then at 25° C. for 1 hour. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was heated at 80° C. for 1.5 hours to give the title compound (11.5 g, 81.2%), which was recrystallized from ethyl acetate/n-hexane to give the pure product, mp 105°-106° C.

Provenance & Evidence