Triethylamine → 4-Benzyloxy-1-butyloxycarbonylamino-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

12.4 ml (93.6 mmol) of butyl chloroformate in 80 ml of acetone are added to a solution of 24.3 g of 3-nitro4-benzyloxybenzoic acid (J. Med. Chem. 1967 (10) 462) and 8.7 g (86.4 mmol) of triethylamine in 200 ml of acetone at 0° C. The mixture was stirred at -5° C. for a further hour, 7.0 g (108 mmol) of sodium azide in 100 ml of water are then added dropwise and the mixture is stirred at 0° C. for 2 hours. The mixture is subsequently introduced onto 800 ml of ice-water and the precipitate which has separated out is filtered off with suction and then introduced into 300 ml of boiling n-butanol.

Provenance & Evidence