Trichloroacetyl isocyanate → Cefuroxime Sodium

Participants

Reaction Steps

A mixture of THF (130 ml), dichloromethane (45 ml), and trichloroacetyl isocyanate (9.3 ml) was protected from moisture and cooled to -10°.To the stirred mixture was added (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid (20 g) in one charge followed by THF (40 ml). The mixture was stirred for 10 minutes at 0° to +5° and then warmed to 22° , There was then added, in one charge, a solution of sodium 2-ethylhexanoate (20 g) in methanol (40 ml) and, after stirring for1 minute, the mixture was left undisturbed at 25° for 2 hours to crystallise. The crystalline material was collected by filtration, washed with ethanol (2×100 ml), and dried in vacuo at 35° to give sodium cefuroxime (24.1 g). The isolated product was shown by G.L.C. to contain 5.3% w/w of ethanol, 0.6% w/w of THF, and 0.04% w/w of methanol.

Provenance & Evidence