Sodium Chloride → HCID 56605540, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-[(3S,4R)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (180 mg) and allyltrimethylsilane (0.12 ml) in dichloromethane (2 ml) was added silver tetrafluoroborate (240 mg) at -78° C. under a nitrogen atmosphere. The stirring mixture was allowed to warm to 0° C. during 45 minutes and kept at the same temperature for one hour. The mixture was diluted with ethyl acetate (10 ml) and a saturated aqueous sodium chloride was added. The mixture was neutralized with a saturated aqueous sodium bicarbonate, diluted with additional ethyl acetate (20 ml) and filtered through a pad of cellurose powder. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (11 g) eluting with 3-30% ethyl acetate in dichloromethane to give methyl 3-methyl-2-[(3S,4R)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxo-4-allylazetidin-1-yl]but-2-enoate (47 mg).

Provenance & Evidence