Phosphate → HCID 53833434, compound

Participants

Reaction Steps

To a stirred solution of 240 mg (0.5 mmol) of azetidinone prepared in Example 1 in 8 ml of 8:1 acetone-water and 2 drops of pH 7 0.1 N phosphate buffer at 25° C. is added 79 mg (0.5 mmol) of solid KMnO4. The mixture is stirred under N2 at 25° for 8 minutes and an additional 79 mg (0.5 mmol) of KMnO4 is then added. The mixture is stirred further for 45 minutes and diluted with EtOAc. The mixture is treated with sufficient aqueous sodium thiosulfate to destroy any remaining permanganate. The mixture is then filtered through celite and washed thoroughly with ethyl acetate. The filtrate is partitioned between EtOAc/brine and the organic phase is separated, dried (MgSO4), filtered and evaporated. Purification of the residue by plate layer chromatography affords 4-acetoxy-3-methoxy-3-phenylacetamido-azetidin-2-one (1). ##STR39##

Provenance & Evidence