Trifluoroacetic acid → HCID 68131874, compound

Participants

Reaction Steps

To 100 ml. of a solution of trifluoroacetic acid in methylene chloride (0.297 ml. trifluoroacetic acid in 125 ml. methylene chloride) at 0° C. was added 1.048 g. of a mixture of benzhydryl 7-(2-thienylacetamido)-3-(3-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate and the corresponding 3-cephem compound. After 6 hours a saturated aqueous sodium bicarbonate solution was added, and the mixture was allowed to warm to room temperature. The organic layer was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous MgSO4, and evaporated in vacuo to dryness. The foam thereby obtained was dissolved in methylene chloride; 59 mg. of 7-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid lactone (the product derived from the 3-cephem starting material) crystallized and was filtered. The filtrate was concentrated in vacuo and cooled. Another 209 mg. of lactone, mixed with some of the title product, was obtained. Evaporation in vacuo to dryness of the resulting solution provided 680 mg. of the title product: nmr (acetone D-6 ) δ3.85 (s, 2, side chain CH2), 4.17 (s, 2, --CH2OH), 5.25 (d, 1, J = 4.5 Hz, C6 --H), 5.54 (dd, 1, J = 4.5 and 8.0 Hz, C7 --H), 6.40 (bs, 1, C2 --H), 6.95 (s, 1, ester CH), 7.32 (m, 13, thienyl + ArH), and 8.04 (d, 1, J = 8.0 Hz, side chain NH).

Provenance & Evidence