Acetic Acid → HCID 13362788, compound

Participants

Reaction Steps

A solution of 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)acetamido]-3-cephem-4-carboxylate (1.4 g) in a mixture of methanol (25 ml) and tetrahydrofuran (60 ml) was added to a mixture of 10% palladium-on-carbon (1.7 g), glacial acetic acid (7 ml) and methanol (20 ml) in an atmosphere of nitrogen. Hydrogen gas was introduced into the mixture and shaken for 8.5 hours at room temperature. After removing the insoluble substance by filtration, the filtrate was concentrated under reduced pressure. The residue was pulverized with diethyl ether, and the resultant substance was dissolved in an aqueous solution of sodium bicarbonate, washed with ethyl acetate and diethyl ether in turn and then the remaining ether was removed by bubbling with nitrogen gas. The resultant solution was adjusted to pH 4.5 with dilute hydrochloric acid, subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries Ltd.), and eluted with 20% isopropyl alcohol. Isopropyl alcohol was distilled off under reduced pressure and the remaining solution was lyophilized to give 7-[2-(2-amino-4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (185 mg).

Provenance & Evidence