Triphenylphosphine → HCID 88802658, compound

Participants

Reaction Steps

A solution of diphenylmethyl 3-iodomethyl-7β-(2-thienylacetamido)ceph-3 -em-4-carboxylate (30 g.,) Rf 0.6 in ethyl acetate (500 ml.) was stirred in the dark at room temperature and treated, over 45 minutes, with a solution of triphenylphosphine (24.9 g., ca. 2 equivs.) in ethyl acetate (150 ml.). The mixture was stirred for a further 60 minutes at 0°, and the precipitated solid collected by filtration. The solid was washed with ethyl acetate and dried in vacuo to give the phosphonium iodide (31.7 g., 74.5%), Rf 0.0, m.p. 142°-146° (decomp.), [α]D + 10° (tetrahydrofuran), λmax 269 nm (ε9,400) and 276 nm (ε8,600) νmax (CHBr3) 3350 (NH), 1780 (β-lactam), 1710 (CO2R), 1680 and 1505 (CONH), and 1445 (P-C(aryl)) cm-1, τ (CDCl3) 4.39 (C(7) -H,dd,J 4.5 and 9 Hz), 5.19 (C(6) -H, d, J 4.5 Hz) 4.75 and 4.85 (CH2 -P, four major signals of two AB-q JP-H 16 Hz), 6.05 and 6.68 (C(2) - CH2 two dd, JH-H 18 Hz, JP-H 3-4 Hz). [Found: C, 59.3; H, 4.5; I, 13.4; N, 2.6; P, 3.4; S, 7.3. C45H38IN2O4PS2 (892.8) requires C, 60.5; H, 4.3; I, 14.2; N, 3.1; P, 3.5; S, 7.2%].

Provenance & Evidence