Isopropanol → [(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxoazetidin-2-yl]acetic acid

Participants

Reaction Steps

A solution of (6R,7R)-2,2-dimethyl-7-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-aza-3-oxabicyclo[4.2.0]octan-8-one (11.99 g) in acetone (119.9 ml) was added dropwise to a solution of 2N Jones reagent (38.13 ml) in acetone (119.9 ml) at ambient temperature over a period of an hour, and the mixture was stirred for an additional 30 minutes. After addition of an excess of isopropyl alcohol to the mixture, the solvent was removed by evaporation. The residue was dissolved in ethyl acetate (1 l) and the solution was washed with water. The aqueous washings were extracted with ethyl acetate (200 ml). The organic layers were combined, washed with an aqueous sodium chloride, dried over magnesium sulfate, and evaporated to give 2-[(2R,3R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-4-oxo-azetidin-2-yl]acetic acid (11.8 g).

Provenance & Evidence