HCID 14460291, compound → HCID 23035702, compound

Participants

Reaction Steps

A solution of 0.33 ml of thioacetic acid in 4.5 ml of 1N sodium hydroxide solution is added dropwise at room temperature under a nitrogen atmosphere to a solution of 438 mg (3.06 mmoles) of 4-acetoxy-3-methylazetidin-2-one (produced according to K. Clauss et al., Lieb, Ann. Chem., 1974, 539; racemic mixture of cis- and trans-isomer in a ratio of 3:1; Mp 53°-65°) in 1.13 ml of water and 0.27 ml of acetone, and the mixture is stirred at the same temperature for 3 hours. The reaction mixture is exhaustively extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed over silica gel with toluene/ethyl acetate (4:1 to 3:2) and yields first of all the pure trans-compound, then a mixture of the cis- and trans-isomers of the title compound and subsequently the pure cis-compound.

Provenance & Evidence