Hydrochloric Acid → 7-[2-Ethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

Participants

Reaction Steps

A mixture of 7-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.4 g) in methanol (20 ml) and conc. hydrochloric acid (0.85 g) were stirred for 2.5 hours at room temperature. The reaction mixture was added to a mixture of water and ethyl acetate. The aqueous layer was separated, washed with ethyl acetate and adjusted to pH 4.0 with 10% aqueous solution of sodium hydroxide. The resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries) and eluted with 5% aqueous solution of isopropyl alcohol. The fractions containing the object compound were concentrated and lyophilized to give 7-[2-ethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.35 g).

Provenance & Evidence