Hydrochloric Acid → HCID 131714500, compound

Participants

Reaction Steps

A mixture of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-[3-(4-methyl-1-piperazinyl)propyl]-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (1.1 g), methanol (85 ml) and conc.hydrochloric acid (0.6 ml) was stirred for 45 minutes at room temperature. The reaction mixture was adjusted to pH 4.5 with a saturated aqueous solution of sodium bicarbonate and then concentrated. The concentrate was adjusted to pH 7 with a saturated aqueous solution of sodium bicarbonate and then subjected to column chromatography (CM-cephadex, H-type: 110 ml), eluted with 1%, 2%, 4% and 5% aqueous solution of sodium chloride The fractions containing the object compound were collected and adjusted to pH 4.3 with a saturated aqueous solution of sodium bicarbonate. The resulting solution was subjected to column chromatography (Non-ion adsorption resin, Diaion HP20 prepared by Mitsubishi Chemical Industries: 50 ml), eluting with water and 20% isopropyl alcohol. The fractions containing the object compound were collected and concentrated under reduced pressure. The concentrate was lyophilized to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-[3-(4-methyl-1-piperazinyl)propyl]-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.3 g).

Provenance & Evidence