Oxygen → p-Toluenesulfonate

Participants

Reaction Conditions

Reaction Steps

A stream of oxygen and ozone (containing 0.35 mmol of ozone per minute) is passed for 4 minutes through a solution, cooled to -60° C, of 0.553 g of the 4-methylphenylsulphonate of 7β-amino-3-methylene-cepham-4α-carboxylic acid diphenylmethyl ester in 50 ml of methanol. After a further 5 minutes, the pale blue-coloured solution is treated with 0.3 ml of dimethyl sulphide. The mixture is stirred for 15 minutes at -70° C, for 1 hour at -12° C and for 1 hour in an ice bath and is then evaporated. The residue is taken up in a small amount of methylene chloride, diethyl ether is then added until the mixture turns cloudy, and the mixture is left to stand. The microcrystalline, reddish-coloured pulverulent precipitate is filtered off and yields the 4-methylphenylsulphonate of 7β-amino-cepham-3-one-4α-carboxylic acid diphenylmethyl ester which is mainly present in the enol form as the 4-methylphenylsulphonate of 7β-amino-3-cephem-3-ol-4-carboxylic acid diphenylmethyl ester, melting point = 143°-145° C (with decomposition); thin layer chromatogram (silica gel) Rf ~0.28 (system: ethyl acetate/pyridine/water, 85:10:5); ultraviolet absorption spectrum (in ethanol): λmax = 262 mμ (ε= 3,050) and 282 mμ (ε= 3,020); infrared absorption spectrum (in methylene chloride): characteristic bands at 5.58 μ, 5.77 μ (shoulder), 6.02 μ and 6.22 μ.

Provenance & Evidence