HCID 88802391, compound → HCID 70616346, compound

Participants

Reaction Steps

2,2,2-Trichloroethyl 7β-formamido-3-vinylceph-3-em-4-carboxylate (0.88 g., 2.3 mmole) was treated with dry methanol (5 ml.), when some solid crystallised. The suspension was cooled to ca. 5° and stirred while phosphorus oxychloride (0.53 ml.) was added dropwise. The reaction mixture was kept at ca. 5° for 30 minutes and diluted with ether (20 ml.); no solid separated. The solvents were evaporated and the residual oil was treated with ether (ca. 10 ml.) to give a white solid. The solid was filtered off, washed with ether, and dried to give the title hydrochloride (0.765 g., 85%), λmax. (MeOH) 295 nm (ε 10,150), νmax. (Nujol), ca. 2590 (N+H3), 1788 (azetidin-2-one), 1730 (CO2R), and 946 cm-1 (=CH2), τ (Me2SO-d6), 2.86 (1H, dd, J 11 and 17.5 Hz; CH=CH2), 4.13 (1 H, d, J 17.5 Hz) and 4.45 (1H, d, J 11 Hz) (CH=CH2), 4.64 (1H, d, J 5 Hz; C7 -H), 4.78 (1H, d, J 5 Hz; C6 -H), 4.81 and 4.98 (2H, AB-q, J 12 Hz; CH2CCl3), 5.92 and 6.24 (2H, AB-q, J 17 Hz; C2 -H2), 6.31 (ca 1H, d, JP-H 11 Hz; ca. 0.1 M trimethyl phosphate) (Found: P, 0.78%).

Provenance & Evidence