反应详情

A mixture of (3S,4S)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-acetoxy-azetidin-2-one (1.67 g, 3.95 mmole), 1,3-dibromo-2-propanol (689 mg, 3.16 mmole), and zinc acetate dihydrate (435 mg, 1.98 mmole) in a mixture of benzene (25 ml) and toluene (25 ml) was refluxed overnight using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate (200 ml), acetone (40 ml) and water (150 ml). The organic layer was washed with water, brine and dried over sodium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography using ethyl acetate-hexane (4:3) as eluent and (3S,4S)-3-{N-(3-phenylpropionoyl)-L-phenylalanyl}amino-4-(1,3-dibromoprop-2-yl)oxy-azetidin-2-one was obtained (170 mg, 7% yield).

1. temperaturewas refluxed overnight
2. temperatureAfter cooling
3. customthe reaction mixture was partitioned between ethyl acetate (200 ml), acetone (40 ml) and water (150 ml)
4. washThe organic layer was washed with water, brine
5. dry with materialdried over sodium sulfate
6. customAfter removal of the solvent
7. customthe residue was purified by silica gel column chromatography