Hydrochloric Acid → 4-Methylmorpholine

Participants

Reaction Conditions

Reaction Steps

To a solution of 250 mg. (0.5 mmole) of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidine hydrazide in 8 ml. of dimethylformamide was added 0.42 ml. of a 4N solution of hydrochloric acid in dioxane, and the mixture was cooled to -60° C. 0.1 ml. of isopentyl nitrite was then added and the reaction temperature was raised to -20° C. After disappearance of the hydrazide had been confirmed, the temperature was lowered to -60° C. The mixture was neutralized with 0.17 g. of N-methylmorpholine to form a solution of N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidine azide.

Provenance & Evidence