N-carbobenzyloxyalanine → HCID 67694773, compound

Participants

Reaction Steps

A mixture of 1.5 g of 2-[3-cycloheptyl-3-(4-dimethylaminophenyl)ureido]-4-methoxy-6-tert-butylphenol, 2.16 g of N-benzyloxycarbonyl-L-alanine, 1.95 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), 0.62 g of 4-dimethylaminopyridine (DMPA) and 30 ml of dimethylformamide (DMF) was stirred at room temperature for 5 hours. A saturated saline solution was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed and dried. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 1.3 g of O-(N-benzyloxycarbonyl-L-alanyl)-2-[3-cycloheptyl-3-(4-dimethylaminophenyl)ureido]-4-methoxy-6-tert-butylphenol (yield: 60%, melting point: 126° C.).

Provenance & Evidence