1,4-Dioxane → (3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

Participants

Reaction Steps

1.5 equivalents of an aqueous sodium thioacetate solution are added to a solution of 40 mg of (3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidine (for manufacture see below) in 1.5 ml of phosphate buffer of a pH of 7 and 0.1 ml of dioxan, and the mixture is stirred for 30 minutes at room temperature. The reaction mixture is extracted with methylene chloride and the separated organic solution is then dried over sodium sulphate. The solvent is evaporated off in vacuo and the residue is purified by chromatography over silica gel with toluene/ethyl acetate (3:1). The IR spectrum of the resulting title compound (in methylene chloride) is identical to that of the product obtained according to a).

Provenance & Evidence