Thiophenol → HCID 131710157, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (-10° C.), stirred solution of benzhydryl 7-(2-thienylacetamido)-3-carboxy-2-cephem-4-carboxylate (.267 g., 0.5 mmol.) in 25 ml. of methylene chloride under an argon atmosphere was added 0.152 g. (1.5 mmol.) of N-methylmorpholine. The reaction mixture was then cooled to -20° C. and 0.135 g. (1.25 mmol.) of ethyl chloroformate was added. The mixture was stirred at 0° for 30 minutes after which time the mixture was cooled to -10° and 0.165 g. of thiophenol was added. After stirring the reaction mixture at 0° for 1 hour, ethyl acetate was added, and the resulting solution was washed successively with aqueous sodium bicarbonate, water, and brine and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness gave a product which was chromatographed on a silica gel column using a tolueneethyl acetate gradient to provide 0.208 g. (66.5%) of the title product: ir (CHCl3) 1798 cm-1 (β-lactam C = 0); nmr (CDCl3) 3.80 (s, 2, side chain CH2), 5.06 (d, 1, J = 4.0 Hz, C6 --H), 5.42 (q, 1, J = 4.0 and 8.0 Hz, C7 --H), 5.70 (s, 1, C4 --H) and 7.87 ppm (s, 1, C 2 --H).

Provenance & Evidence