Water → HCID 14672333, compound

Participants

Reaction Conditions

Reaction Steps

(a-1) To a solution of 16.5 g (31.3 mM) of p-methoxybenzyl 7β-phenylacetamido-3-methanesulfonyloxy-3-cephem-4-carboxylate in 70 ml of N,N-dimethylformamide were added a solution of 2.75 g (34.4 mM) of 70% sodium hydrosulfide in 30 ml of N,N-dimethylformamide and 6.06 g (47.0 mM) of diisopropylethylamine at -20° C., and the mixture was stirred at 0° C. for one hour. After the reaction, 1 l of water was added, the mixture was washed with ethyl acetate (200 ml×3), and the aqueous layer was adjusted to pH 1 with 3% hydrochloric acid and extracted with ethyl acetate (500 ml and 200 ml). The extract was washed with a saturated aqueous sodium chloride solution (300 ml×2) and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was dissolved in 200 ml of dichloromethane, and the solution was added dropwise to 700 ml of diethyl ether with stirring. The precipitate formed was collected by filtration to give 7.24 g of p-methoxybenzyl 7β-phenylacetamido-3-mercapto-3-cephem-4-carboxylate.

Provenance & Evidence