Sodium Hydroxide → HCID 53998408, compound

Participants

Reaction Steps

A solution of [4-diphenylmethoxycarbonyl-7β-(2-thienylacetamido)ceph-3-em-3-ylmethyl] triphenylphosphonium iodide (25 g.) in acetone (300 ml.) with water (40 ml.) was cooled to 0° and taken to pH 11 with 2N-sodium hydroxide. The mixture, containing a precipitated yellow solid, was diluted with acetone (200 ml.) and water (50 ml.), and filtered. The collected solid was washed with acetone and ether, and dried in vacuo to give diphenylmethyl 7β-(2-thienylacetamido)-3-(triphenylphosphoranylidenemethyl)ceph-3-em-4-carboxylate (17 g., 78.5%) as a yellow crystalline solid, m.p. 133°-138° (Decomp), [α]D - 35° (CHCl3), λmax (CHCl3) 388 nm. (ε 18,500), 273 nm (ε6,240) and 267 nm (ε6,940), νmax (CHBr3) 3360 (NH), 1746 (β-lactam), 1670 (CO2R), 1642 and 1500 (CONH), and 1438 (P-C aryl) cm-1 ; τ(CDCl3) 4.82 (C(7) --H, dd, J 4.5, 9Hz), 4.95 (C(6) --H,d, J 4.5 Hz), 7.11 and 7.55 (C(2) --CH2, two dd. J 14 Hz., JP-H 1-2 Hz) and 4.5 ##STR34## [Found: C, 66.6; H, 4.7, N, 2.9; P, 3.9; S, 7.8. C45H37N2O4S2P (764.8) requires C, 70.6; H, 4.8; N, 3.6; P, 4.0; S, 8.4%[.

Provenance & Evidence