Acetic Acid → HCID 57134054, compound

Participants

Reaction Steps

91 mg (0.24 mmole) of (3S, 4R)-3-[(R)-1-benzoyloxyethyl]-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2-one were dissolved in 1 ml of methanol. To the resulting solution was added a solution of 7.17 mg (0.31 mmole) of sodium in 0.65 ml of methanol at 0° C., and then the mixture was stirred at room temperature (18°-20° C.) for 5 hours. After completion of the reaction, the mixture was made slightly acidic by the addition of acetic acid, diluted with 20 ml of ethyl acetate and washed with water. After drying the mixture, the solvent was distilled off. The resulting residue was subjected to preparative thin layer chromatography on silica gel developed with a 2:1 by volume mixture of benzene and ethyl acetate to give 50 mg (yield 74.4%) of the pure product as an oil, which was proved by nuclear magnetic resonance spectroscopy to be an approximately 4:1 mixture of the 1'R- and 1'S-isomers.

Provenance & Evidence