Hydrochloric Acid → HCID 14052429, compound

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A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(E)-3-acetoxy-1-propenyl)-3-cephem-4-carboxylate (1.98 g, 1.75 mmol) in formic acid (20 ml) was stirred for 2 hr at room temperature. Conc. hydrochloric acid (0.16 ml, 1.92 mmol) was added to the mixture and the mixture was stirred for 1 hr at room temperature. Filtration, and concentration of the filtrate, followed by trituration with IPE gave 975 mg of the crude product. Chromatography on a column of reversed phase silica gel and elution with 10% MeOH in water and concentration of the fraction containing the desired product gave 418 mg (51%) of the title compound as an amorphous powder. IR νmax (KBr) cm-1 1765, 1730, 1650. UV λmax (pH 7 phosphate buffer) nm (ε) 290 (23400). 1H NMR (DMSO-d6) δ 2.03 (3H, s, OAC), 3.65 (2H, ABq, 2-H), 4.61 (2H, ABq, CH2OAc), 5.15 (1H, d, J=5 Hz, 6-H), 5.75 (1H, dd, J=5 & 8 Hz, 7-H), 6.15 (1H, m, vinyl-H), 6.65 (1H, s, thiazole), 6.85 (1H, d, J=15 Hz, vinyl-H), 7.05 (2H, s, NH2).

Provenance & Evidence