Hydrochloric Acid → HCID 178445969, compound

Participants

Reaction Steps

To a suspension of 66 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 5 ml of dry N,N-dimethylformamide were added successively 0.08 ml of a dry 5.1N-hydrogen chloride in N,N-dimethylformamide solution and 0.02 ml of isoamyl nitrite at -20° C. with stirring, and the mixture was stirred under ice-cooling. After disappearance of hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.06 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine azide. The azide solution was added dropwise to a solution of 40 mg of (3S)-N-benzyl-3-amino-2-hydroxy-5-methylhexylamine dihydrochloride and 0.018 ml of triethylamine in 2 ml of dry N,N-dimethylformamide under ice-cooling, and the mixture was stirred for 16 hours under ice-cooling. The reaction mixture was evaporated under reduced pressure, and a 5% aqueous sodium bicarbonate solution was added to the residue. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: chloroform/methanol=15/1 by volume) to obtain 33 mg of (2RS, 3S)-N-benzyl-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl}amino-2-hydroxy-5-methylhexylamine as a white powder.

Provenance & Evidence