Isopropanol → 2-[(2R, 3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid

Participants

Reaction Steps

A solution of (3R, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (250 mg) in acetone (26.7 ml) as added to a solution of 2N Jones reagent (2.67 ml) in acetone (24.03 ml) at ambient temperature over a period of 40 minutes and the mixture was stirred for another 40 minutes. After addition of an excess of isopropyl alcohol to the mixture, the solvent was distilled off. The residue was dissolved in chloroform and washed with a saturated aqueous sodium chloride. The aqueous layer was extracted four times with chloroform. The extracts were combined, dried over magnesium sulfate, filtered and evaporated. The crystalline residue was washed with hexane to give 2-[(2R, 3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid (211 mg).

Provenance & Evidence