Imidazole → HCID 19099269, compound

Participants

Reaction Steps

To a stirred solution of 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)butan-3-ol (90.00 g) in N,N-dimethylformamide (800 ml) were added imidazole (85.51 g) and t-butyldimethylsilyl chloride (61.53 g). The resulting mixture was allowed to stand at ambient temperature for 14 hours. The mixture was diluted with ethyl acetate (2.4 l), washed successively with water (1.6 l) and brine (1 l), and dried over magnesium sulfate. Removal of the solvents gave a residue, which was chromatographed on silica gel (1 l) eluting with a mixture of n-hexane and ethyl acetate (9:1-7:3, V/V) to give 1-allyloxycarbonylamino-2-(N-allyloxycarbonylaminomethyl)-3-(t-butyldimethylsilyloxy)butane (115.40 g).

Provenance & Evidence