Hydrazine hydrate (1:1) → HCID 13622584, compound

Participants

Reaction Steps

A mixture of tert-butyl 3(S)-[1(S)-ethoxycarbonyl-6-phthalimidohexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.65 g), hydrazine hydrate (0.27 g) and ethanol (10 ml) is allowed to stand overnight at room temperature. The mixture is concentrated in vacuo, diluted with water (50 ml) and extracted with ethyl acetate (50 ml×4). To a mixture of the organic extract, water (50 ml) and sodium bicarbonate (0.65 g) are added dropwise di-tert-butyl dicarbonate (0.36 g) with stirring at room temperature. After stirring for 30 minutes, the ethyl acetate layer is separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is subjected to silica gel column chromatography using hexane:ethyl acetate (2:1-1:1) as an eluent to yield tert-butyl 3(S)-[6-tert-butoxycarbonylamino-1(S)-ethoxycarbonylhexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (0.54 g) as a colorless oil.

Provenance & Evidence