Dicyclohexylcarbodiimide → 3-[2-(Benzyloxycarbonylamino)propionyl]-2,2-dimethyl-5-oxo-1-imidazolidineacetamide

Participants

Reaction Conditions

Reaction Steps

To a stirred, ice cold solution of N-(benzyloxycarbonyl)alanine (6.7 g) and 2,2-dimethyl-5-oxo-1-imidazolidineacetamide (5.2 g) in 100 ml of dimethylformamide (DMF), a solution of dicyclohexylcarbodiimide (DCC) (6.2 g) in 50 ml of DMF was added dropwise during 15'. The suspension was stirred at 0° C. for 2 hours and at room temperature for additional 2 hours. The insoluble material was filtered off, the solvent was evaporated under reduced pressure, affording crude 3-[2-(benzyloxycarbonylamino)propionyl]-2,2-dimethyl-5-oxo-1-imidazolidineacetamide m.p. 206°-210° C. Into a solution of this compound (3 g) in methanol (100 ml) containing 5% palladium on charcoal (0.6 g) hydrogen was bubbled at 20° C. for 1.5 hours. Removal of catalyst and evaporation of the solvent gave a residue which was triturated with ethanol to afford the title compound, m.p. 196°-197° C.

Provenance & Evidence