Diisopropyl Ether → HCID 131714494, compound

Participants

Reaction Steps

To the mixture containing 7-[2-methoxyimino-2-(2-dimethoxyphosphorylaminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) was dropped trimethylsilyl bromide (14.80 g) at 3° to 8° C. under stirring, which was continued for 2.5 hours at ambient temperature. The reaction mixture was poured into diisopropyl ether (1.5 l) and the resultant resinous oil was separated by decantation. The oil was dissolved in water (300 ml), adjusted to pH 1 with 1N hydrochloric acid and subjected to column chromatography on a nonionic adsorption resin "Diaion HP-20" (320 ml). After the column was washed with water (1.4 l), the elution was carried out with 20% aqueous methanol. The fractions containing the object compound were collected, evaporated to remove methanol and lyophilized to give 7-[2-methoxyimino-2-(2-phosphonoaminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.3 g), mp. 155° to 164° C. (dec.).

Provenance & Evidence