Water → 2,4,6-Trimethylbenzenesulfonic acid

Participants

Reaction Steps

In 50 ml of anhydrous methylene chloride was suspended 6.94 g of 2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminothioacetic acid-S-methyl ester, and 4.26 g of boron trifluoride-diethyl ether complex was added with ice-cooling to the resulting suspension to form a solution. Then, 40 ml of an anhydrous methylene chloride solution containing 4.10 g of pivaloyloxymethyl 7-amino-3-[2-(5-methyl-1,2,3,4-tetrazolyl)]methyl-Δ3 -cephem-4-carboxylate was added to the solution, and the resulting mixture was subjected to reaction at room temperature for 7 hours. The reaction mixture obtained was introduced into 50 ml of water, and the organic layer was separated. Then, 50 ml of water was added to the organic layer, and the pH was adjusted to 0.5 with 6N hydrochloric acid. Then, the organic layer was separated, and 50 ml of water was added thereto. The pH was adjusted to 5.0 with sodium hydrogencarbonate. The organic layer was further separated, washed with 50 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under reduced pressure, the residue obtained was dissolved in 80 ml of ethyl acetate. Then, 2.36 g of mesitylenesulfonic acid dihydrate was added to the resulting solution, and stirred for 30 minutes, and the precipitated crystals were collected by filtration to obtain 7.05 g (yield, 88.8%) of mesitylenesulfonic acid salt of pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-[2-(5-methyl-1,2,3,4-tetrazolyl)]methyl-Δ3 -cephem-4-carboxylate having a melting point of 218°-220° C. (decomp.).

Provenance & Evidence