Hydrochloric Acid → N-[N-(3-butanoyloxyhexanoyl)glycyl]-L-serine

Participants

Reaction Steps

3-Butanoyloxyhexanoic acid (234 mg) prepared by the method described in Preparation 6-(2) and N-hydroxysuccinimide (133 mg) was dissolved in dioxane (3 ml). N,N'-Dicyclohexylcarbodiimide (239 mg) was added thereto under ice cooling. The mixture was reached to room temperature and stirred at ambient temperature over night. The crystallized N,N'-dicyclohexyl urea was filtered off and the filtrate was concentrated to give a residue which was dissolved in N,N-dimethylformamide (5 ml). To this solution was added a solution of N-glycyl-L-serine (324 mg) and triethylamine (280 μl) in water (3 ml) at 0° C. The resulting mixture was reached to room temperature and stirred at ambient temperature overnight. The reaction mixture was acidified with 1 N hydrochloric acid, extracted with ethyl acetate, washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off to give a residue which was subjected to preparative thin layer chromatography (Merck, 0.25 mm×5) and eluted with a mixture of benzene, dioxane and acetic acid (10:5:1). The band containing the object compound was extracted with a mixture of methanol and chloroform (3:7) and the solvent was evaporated off under reduced pressure to afford a wax of N-[N-(3-butanoyloxyhexanoyl)glycyl]-L-serine.

Provenance & Evidence