Metaperiodic acid → HCID 67867010, compound

Participants

Reaction Steps

To a solution of (3S,4R)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-1-(ethoxalyl)-4-[(1R)-3-hydroxy-1,3-dimethyl-2-oxobutyl]-2-azetidinone (50 mg) in methanol (2 ml) was added 0.54M aqueous periodic acid solution (1.0 ml). After stirring at room temperature for 5 hours, the solvent was removed in vacuo and the residue was extracted with dichloromethane. The extract was dried over magnesium sulfate and evaporated to afford (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-1-(ethoxalyl)-4-oxoazetidin-2-yl]propionic acid (93 mg). To a solution of the compound obtained above in diethyl ether (2 ml) was added a solution of diazomethane in diethyl ether at room temperature. The solvent was removed in vacuo and the residue was chromatographed on silica gel (1 g) eluting with a mixture of ethyl acetate and hexane (1:5, V/V) to give methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-1-(ethoxalyl)-4-oxoazetidin-2-yl]propionate (24 mg).

Provenance & Evidence