Water → HCID 57228824, compound

Participants

Reaction Steps

A mixture of (3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)amino-4-acetoxy-azetidin-2-one (4.57 g, 10.8 mmole), 2-bromoethanol (1479 mg, 11.83 mmole), and zinc acetate dihydrate (1.78 g, 8.128 mmole) in a mixture of benzene (150 ml) and toluene (150 ml) was refluxed for 7 hrs using Dean-Stark water separator. After cooling, the reaction mixture was partitioned between ethyl acetate (1000 ml), acetone (100 ml) and water (500 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 (55:45) as eluent and (3S,4S)-3-(N-benzyloxycarbonyl-L-phenylalanyl)amino-4-bromoethoxy-azetidin-2-one was obtained (650 mg, 12% yield).

Provenance & Evidence