p-Toluenesulfonic acid → HCID 13127405, compound

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The toluene-p-sulphonic acid salt of diphenylmethyl (6R,7R)-7-amino-3-trichloroacetylcarbamoyloxymethylceph-3-em-4-carboxylate (17.2 g, 22.7 mmole) was dissolved in a mixture of anhydrous methanol (900 ml) and acetyl chloride (45 ml) and left to stand at 20° for 5 hours. Removal of the solvent under reduced pressure gave an oil, which was dissolved in dichloromethane. This solution was shaken with aqueous sodium bicarbonate solution and then washed with water. Toluene-p-sulphonic acid monohydrate (4.3 g, 22.7 mmole) was added and the solvent was evaporated in vacuo. The residue was dissolved in hot isopropanol (ca. 150 ml) and the solution was poured into diisopropyl ether (ca. 600 ml). The precipitated solid was filtered off and dried in vacuo to give the title compound (8.9 g, 64%), m.p. 110° to 112°; [α]D21° -14° (c, 1.0 in CHCl3); λmaxEtOH 259 nm (ε 6,120) and λinf.EtOH 227 nm (ε 15,800).

Provenance & Evidence