Ethanol → allyl [(3S,4S)-2-oxo-4-[(R)-3-oxo-1,4-dithian-2-yl]-3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-1-yl]glyoxylate

Participants

Reaction Conditions

Reaction Steps

A solution of (3S,4S)-3-[(R)-1-(trimethylsilyloxy)-ethyl]-4-[(R)-3-oxo-1,4-dithian-2-yl]azetidin-2-one (650 mg), prepared in Reference Example 14, in dichloromethane (10 ml) was cooled at 0° C. and a solution of pyridine (483 mg) in dichloromethane (2 ml) and a solution of allyl chloroglyoxylate (603 g) in dichloromethane (3 ml) were added. The mixture was stirred at the same temperature for 2 hours. To this mixture was added ethanol (187 mg) at 0° C. and the mixture was stirred for 10 minutes, after which ether (30 ml) was added. The organic layer was washed with water, saturated copper sulfate solution and saturated aqueous sodium chloride solution in the order mentioned and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (packing: silica gel; ethyl acetate-hexane=1:5). The procedure gave allyl [(3S,4S)-2-oxo-4-[ (R)-3-oxo-1,4-dithian-2-yl]-3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-1-yl]glyoxylate as a colorless oil (853 mg).

Provenance & Evidence