Triethylamine → 2-{[(Benzyloxy)(hydroxy)methylidene]amino}-N-(1,3-diethoxy-1,3-dioxopropan-2-yl)ethanimidic acid

Participants

Reaction Steps

To a suspension of diethyl 2-aminomalonate hydrochloride (10.6 g) in tetrahydrofuran are added N-(benzyloxycarbonyl)glycine (10.5 g) and triethylamine (5.1 g). The mixture is cooled to 0° to 5° C., and thereto is added N,N'-dicyclohexylcarbodiimide (10.8 g). The mixture is stirred at the same temperature for 2 hours and then allowed to stand at room temperature overnight. Insoluble substance is filtered off from the reaction mixture. The filtrate is distilled to remove the solvent, and to the residue is added ethyl acetate, and the insoluble substance is filtered off. The filtrate is concentrated under reduced pressure, and the residue is recrystallized from ethyl acetate-isopropyl ether to give diethyl 2-[[N-(benzyloxycarbonyl)glycyl]amino]malonate (16.0 g), m.p. 94.5°-95.5° C.

Provenance & Evidence