Sulfuric Acid → Cefuroxime Axetil

Participants

Reaction Steps

11.14 g of cefuroxime in the form of a salt with n-butylamine are dissolved at ca. 3° to 5° in 28 ml of dimethyl acetamide. A solution of 7.48 g of acetoxyethyl bromide in 21 ml of dimethyl acetamide is added to the solution obtained, and 1.76 g of K2CO3 are added in portions over the course of ca. 120 minutes. The resulting mixture is stirred for ca. 30 minutes, diluted with 100 ml of EtAc and aqueous 3% NaHCO3 solution is added. Two phases are formed and are separated and the organic phase is washed with 1 n HCl and 20% aqueous NaCl solution, which contains 2% NaHCO3. The organic phase obtained is mixed with 11 ml of dimethyl acetamide and 28 ml of H2O, and the pH of the mixture obtained is adjusted to ca. 4 by addition of H2SO4. The two phases formed are separated and the organic phase is mixed with activated carbon, which is filtrated off. From the filtrate obtained solvent is evaporated off and the evaporation residue obtained is mixed with seed crystals. The suspension obtained is mixed with 125 ml of diisopropyl ether and stirred at room temperature. Crystalline cefuroxime axetil is obtained, filtrated off, washed with a mixture of EtAc and diisopropyl ether and dried. Yield: 7.43 g.

Provenance & Evidence