Hydrazine hydrate (1:1) → HCID 13622588, compound

Participants

Reaction Steps

A mixture of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-8-phthalimidooctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.55 g), hydrazine hydrate (0.22 g) and ethanol (10 ml) is allowed to stand overnight at room temperature. After evaporation of ethanol, the residue is dissolved in water (50 ml) and extracted with ethyl acetate (50 ml×4). Water (50 ml) and sodium bicarbonate (0.6 g) are added to the organic extract, and to the resulting mixture is added dropwise di-tert-butyl dicarbonate (0.29 g) with stirring. After stirring for 30 minutes at room temperature, the ethyl acetate layer is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography using hexane:ethyl acetate (2:1-1:1) as an eluent to give tert-butyl 3(S)-[8-tert-butoxycarbonylamino-1(S)-ethoxycarbonyloctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.48 g) as a colorless oil.

Provenance & Evidence