Dichloromethane → Cefuroxime Sodium

Participants

Reaction Steps

A mixture of THF (60 ml), dichloromethane (25 ml), and trichloroacetyl isocyanate (6.2 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 (10 g) in one charge followed by THF (20 ml). The temperature was controlled in the range 0° to +5° and the mixture stirred for 10 minutes. Ethane-1,2-diol (15 ml) was added followedby a solution of sodium 2-ethylhexanoate (10 g) in THF (20 ml) to raise thepH to 7.3. The mixture was warmed to 25° and left undisturbed for 1 hour. The mixture was then stirred briefly and left undisturbed for a further hour. The crystalline material which had separated from the mixture was collected by filtration, washed with THF (2×50 ml), and dried in vacuo at 35° to yield sodium cefuroxime (10.76 g) THF solvate. The isolated product was shown by G.L.C. to contain 8.8% w/w of THF and 0.56% w/w of ethane-1,2-diol.

Provenance & Evidence