Sulfuric Acid → HCID 13277552, compound

Participants

Reaction Conditions

Reaction Steps

trans i.e. (3S,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.08 g) is dissolved in a mixture of tetrahydrofuran (10 ml) and water (2 ml), and 0.02 g of mercury sulfate and a catalytic amount of concentrated sulfuric acid are added, followed by stirring at 25° C. for 3 hours. After addition of 0.1 g of sodium hydrogen carbonate, the mixture is concentrated to dryness under reduced pressure. The residue is extracted with 50 ml of ethyl acetate and the extract is concentrated to dryness. The residue is dissolved in 10 ml of ethyl acetate, and m-chloroperbenzoic acid (0.2 g) is added, followed by strirring for 50 hours. After addition of 0.2 ml of dimethyl sulfide, and the mixture is stirred further for 30 minutes and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 60% ethyl acetate-40% n-hexane) to give trans i.e. (3S,4R)-4-acetoxy-3-[(R)-1-hydroxyethyl]-2-azetidinone (0.04 g).

Provenance & Evidence