Hydrochloric Acid → HCID 178446399, compound

Participants

Reaction Steps

To a solution of 64 mg of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidine hydrazide in 2 ml of N,N-dimethylformamide were added successively dropwise 0.09 ml of a dry 5.1N-hydrogen chloride in N,N-dimethylformamide solution and 0.022 ml of isoamyl nitrite at -20° C., and the mixture was stirred under ice-cooling. After disappearance hydrazide compound, the reaction mixture was cooled to -30° C., and neutralized by adding 0.063 ml of triethylamine to prepare a solution of N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]--histidine azide. The azide solution was added dropwise to a solution of 40 mg of (2RS, 3S)-N-isoamyl-3-amino-2-hydroxy-5-methylhexylamine dihydrochloride in 2 ml of N,N-dimethylformamide under ice-cooling, and the mixture was stirred for 16 hours under ice-cooling. A 5% aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. 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 preparative silica gel thin layer chromatography (developing solvent: lower layer of chloroform/methanol/water=8/3/1 by volume) to obtain 8 mg of (2RS, 3S)-N-isoamyl-3-{N-[(+)-2-(1-naphthylmethyl)-3-(phenethylcarbamoyl)propionyl]-L-histidyl}amino-2-hydroxy-5-methylhexylamine as a white powder.

Provenance & Evidence