4-Methylmorpholine → Azide

Participants

Reaction Conditions

Reaction Steps

An azide solution was prepared in the same way as in Example 8 using 0.45 g. (1 mmole) of N-benzyloxycarbonyl-L-phenylalanyl-L-histidine hydrazide. To the solution was added 0.20 g. (1 mmole) of 1(R)-amino-3-methylbutylphosphonic acid hemihydrochloride (melting at 267°-269.5°) prepared according to the method of J. R. Chambers and A. F. Isbell [J. Org. Chem., 29, 832 (1964)], followed by 0.11 g. of N-methylmorpholine. The mixture was stirred at 4° C. for 11 days. Insoluble matter was removed by filtration and the filtrate was treated in a conventional manner. There was obtained 0.47 g. of the desired compound as a white powdery solid, melting at 159°-167° C.; [α]22 -15.6° (C=0.5, dimethylformamide).

Provenance & Evidence