Hydrochloric Acid → N-{4(S)-[N-Benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanyl]amino-3(S)-hydroxy-6-methylheptanoyl}-L-isoleucinol

Participants

Reaction Conditions

Reaction Steps

517 mg (1 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-3-(2-thienyl)-DL-alanine hydrazide were dissolved in 10 ml of dimethylformamide, and the solution was cooled down to -60° C. 0.85 ml (3.4 mmole) of 4N hydrogen chloride in dioxane was then added. The temperature of this mixture was elevated to -20° C., and then 0.16 ml (1.19 mmole) of isoamyl nitrile was added and the mixture was stirred for 10 minutes. The reaction product was again cooled down to -60° C., and 0.42 ml (3.82 mmole) of N-methylmorpholine was added for neutralization. Subsequently, 370 mg (1.2 mmole) of 4(S)-amino-3(S)-hydroxy-6-methylheptanoyl-L-isoleucinol hydrochloride were added, and the mixture was stirred for 30 minutes. The reaction product was stirred overnight at 0° C., condensed by evaporation under reduced pressure and purified by thin layer chromatography, using as developing solvent a 99:1 by volume mixture of chloroform and methanol, to yield 100 mg (13.2%) of the title compound melting at 160°-162° C., [α]23 -61.7° (C=0.3, dimethylformamide).

Provenance & Evidence