Pyridine → 4-Acetoxy-3-phenylacetamidoazetidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-acetoxy-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-3-phenylacetamidoazetidin-2-one (709 mg, 1.9 mmol [R. J. Stoodley and N. R. Whitehouse, J. Chem. Soc., Perkin I, 32 (1973).] in 5 ml dimethylformamide, 5 ml pyridine and 1 ml water at 0° C. in an ice-water bath is added 497 mg (3.15 mmol) solid potassium permanganate. The mixture is stirred at 0° C. under a nitrogen atmosphere for 1.0 hour. The mixture is treated with sufficient aqueous sodium thiosulfate to destroy the excess permanganate and is diluted with ethylacetate. The mixture is filtered and the filtrate is partitioned between ethylacetate and dilute aqueous hydrochloric acid. The organic phase is separated and is washed successively with dilute aqueous sodium bicarbonate and brine. The organic phase is dried (MgSO4), filtered, and evaporated. The residue is purified by plate layer chromatography [1 development φH-EtOAc (1:1)] to give 95.1 mg (19%) of 1; nmr (CDCl3) 2.03, 3H(s); 3.5, 2H(s); 4.67; 1H(dd, J=1 Hz,7 Hz); 5.73, 1H(d, J=1 Hz); 7.17, 6H(s); 7.53, 1H(bs). ##STR29##

Provenance & Evidence