Formaldehyde → HCID 88802464, compound

Participants

Reaction Steps

40%-Aqueous formaldehyde solution (10 ml.) and 3%-sodium hydrogen carbonate solution (30 ml.) were added to a vigorously stirred solution of [4-diphenylmethoxycarbonyl-7β-formamidoceph-3-em-3-ylmethyl]-triphenylphosphonium bromide (1.875 g., 2.5 mmole) in methylene chloride (20 ml.). The two-phase mixture was stirred for 25 minutes and the organic phase was washed with 2N-hydrochloric acid and water (20 ml of each), dried (MgSO4), and evaporated to an orange foam (1.68 g.). This foam was chromatographed on Kieselgel G (Merck, 75 g.) with 10- and 17%-acetone in methylene chloride as eluants. The appropriate fractions were combined and evaporated to give the title ester as a pale-yellow crystalline solid (334 mg., 32%), m.p. 148° to 152° (decomp), [α]D23 - 66° (c 1.19; Me2SO), λmax. (EtOH) 295 nm (ε 9,350), νmax. (CHBr3), (NH), 1787 (azetidin-2-one), 1725 (CO2R), and 1696 and 1500 cm-1 (CONH), τ (CDCl3) 1.78 (1H, s; CHO), 2.4 to 2.8 (10 H, m; (C6H5)2CH), 2.96 (1H, dd, J 11 and 18 Hz; CH=CH2), 3.01 (1H, s; (C6H5)2CH), 3.29 (1H, d, J 9 Hz; NH), 4.12 (1H, dd, J 9 and 5 Hz; C7 -H), 4.55 (1H, d, J 18 Hz) and 4.72 (1H, d, J 11 Hz) (CH=CH2), 5.02 (1H, d, J 5 Hz; C6 -H), 6.34 and 6.57 (2H, AB-q, J 18 Hz; C2 -H2).

Provenance & Evidence