Chloroform → HCID 131710677, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (5° C.), stirred solution of 0.363 g. of benzhydryl 7-(2-thienylacetamido)-3-propionyl-2-cephem-4-carboxylate in 30 ml. of chloroform was added dropwise a solution of 0.149 g. of 85 percent m-chloroperbenzoic acid in 3 ml. of chloroform. The reaction was allowed to stir with cooling for one hour, after which time it was washed twice with aqueous sodium bicarbonate solution and twice with brine and then dried over anhydrous sodium sulfate. The solution was then evaporated in vacuo to provide a gel which was dissolved in 15 ml. of dimethylformamide. This solution was cooled for five minutes in an ice bath, removed from the ice bath, and subsequently treated with 0.145 ml. of phosphorous trichloride. This mixture was allowed to stir at room temperature for 45 minutes, after which time it was transferred to a separatory funnel with the aid of ethyl acetate and washed successively with aqueous sodium bicarbonate (2X), water (4X), and brine (2X) and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness gave a product which when chromatographed on silica gel using a toluene-ethyl acetate gradient provided 0.267 g. (74 percent) of the title product as a white solid which crystallized as white needles from methylene chloride/hexane (m.p. 220°-221° decomp.): nmr (DMSO d-6) δ0.80 (t, 3, J = 7.0 Hz, --CH2CH3), 2.5 (m), 3.84 (s, 2, side chain CH2), 5.22 (d, 1, J = 4.0 Hz, C6 --H), 5.92 (q, 1, J = 4.0 and 8.0 Hz, C7 --H).

Provenance & Evidence