Hydrochloric Acid → Cefuroxime

Participants

Reaction Conditions

Reaction Steps

Sodium metal (1.8 gm) was reacted under nitrogen atmosphere with ethyl alcohol (40 ml) at room temperature, resulting in a clear solution of sodium ethoxide. A solution of cefuroxime axetil (20.4 gm, S-isomer >90%, R-isomer <10%) in a mixture of tetrahydrofuran (204 ml) and ethyl alcohol (20 ml) was cooled to −60° C. A solution of sodium ethoxide in ethanol was slowly added to this mixture at −60° C. Progress of the reaction was monitored by high pressure liquid chromatography (HPLC). Stirring was continued until cefuroxime axetil almost disappeared (45 minutes). Thereafter, 15% aqueous hydrochloric acid (20 ml) was added and the solvent was evaporated under reduced pressure at low temperature. Water and ethyl acetate (water-immiscible solvent) were added to the reaction mass (basifying agent) and the pH level was adjusted to 6.0 using 5% aqueous potassium bicarbonate solution. The aqueous layer was separated and acidified with 15% aqueous hydrochloric acid to pH 1.0. The resulting solid was filtered, washed with water and dried to yield cefuroxime (15.2 gm).

Provenance & Evidence