Tetrahydrofuran → HCID 14257300, compound

Participants

Reaction Steps

To a solution of 10 g of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone in 250 ml of methanol is added 100 ml of tetrahydrofuran, followed by addition of 3.45 g of methyl thioglycollate and 32.5 ml of 1N sodium hydroxide under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. The solvent is then distilled off under reduced pressure and 100 ml of ethyl acetate is added. The ethyl acetate layer is separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography using n-hexane-ethyl acetate (3:2). The earlier eluate fractions are combined and concentrated under reduced pressure to give 4.35 g of (3R,4R)-4-[[(methoxycarbonyl)methyl]thio]-3-tritylamino-2-azetidinone.

Provenance & Evidence