Dicyclohexylcarbodiimide → HCID 68137584, compound

Participants

Reaction Steps

To a solution of 0.52 mM of N-(1-methylcyclohexyloxycarbonyl) phenylalanine in 4 ml. acetonitrile is added 0.60 mM alanine methyl ester hydrochloride and 80 microliters of triethylamine. Immediately following addition of the triethylamine, a solution of 0.58 mM of N,N'-dicyclohexylcarbodiimide in 2 ml. of acetonitrile is added and the reaction is allowed to stir overnight at 20°-25°C. Excess N,N'-dicyclohexylcarbodiimide is destroyed by addition of 5 drops of 50% acetic acid. After adding 15 ml. of methylenechloride, the reaction mixture is filtered to remove the dicyclohexylurea formed during the reaction and the filtrate is treated in the following manner: wash with saturated sodium bicarbonate, 50% saturated sodium chloride solution, 0.2 N sulfuric acid saturated with sodium sulfate, twice with 50% saturated sodium chloride solution. Repeat washing cycle with two portions of methylene chloride and dry over sodium sulfate. The solvent is removed and substantially pure N-(1-methylcyclohexyloxycarbonyl) phenylalanine-alanine methyl ester is obtained.

Provenance & Evidence