Sodium Chlorate → methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(2-oxoethyl)azetidin-1-yl]-3-methylbut-2-enoate

Participants

Reaction Steps

A solution of osmium tetroxide (0.61 mg) in water (0.05 ml) was added to a solution of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(prop-2-enyl)azetidin-1-yl]-3-methylbut-2-enoate (58 mg) and sodium chlorate (50 mg) in a mixture of tetrahydrofuran (1 ml) and water (1 ml) and the mixture was stirred for 17 hours at ambient temperature. Sodium periodate (60 mg) was then added and stirring was continued for 30 minutes. The resulting mixture was diluted with brine and extracted with ethyl acetate. The extract was washed successively with brine, brine containing sodium bicarbonate, and brine. The mixture was dried over magnesium sulfate and concentrated under reduced pressure to give an oil, which was chromatographed on silica gel (1.5 g, eluting with 2.5% methanol in dichloromethane) to give 49 mg of methyl 2-[(3R,4R)-3-benzyloxycarbonylamino-2-oxo-4-(2-oxoethyl)azetidin-1-yl]-3-methylbut-2-enoate.

Provenance & Evidence