Ethyl Acetate → HCID 131722866, compound

Participants

Reaction Steps

7β-Tert-butoxycarbonylamino-3-(2-trifluoromethanesulfonyloxyvinyl)-3-cephem-4-carboxylic acid benzhydryl ester (trans isomer) (3.9 g, 6.1 mmol) was dissolved in anhydrous DMF (80 ml), added with 2-mercapto-4-oxo-4H-1-benzothiopyran (3.5 g, 18.3 mmol) and N-ethyldiisopropylamine (0.63 g, 4.87 mmol), successively, and stirred at room temperature under argon gas atmosphere for 24 hours. The reaction product was added with ethyl acetate (350 ml), washed with an aqueous solution of saturated sodium hydrogencarbonate (150 ml×2 times) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (Wago Gel™ C-200, methylene chloride-ethyl acetate (8:1)) to obtain 3.56 g (yield: 85.4%) of 7β-tert-butoxycarbonylamino-3-[2-(4-oxo-4H-1-benzothiopyran-2-yl)thiovinyl]-3-cephem-4-carboxylic acid benzhydryl ester as yellow-red froth.

Provenance & Evidence