HCID 131710432, compound → HCID 54460561, compound

Participants

Reaction Steps

t-Butyl (1R,6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate 1-oxide (syn isomer) (0.42 g) was dissolved in trifluoroacetic acid (5 ml) and stirred at room temperature for 8 minutes. The solution was evaporated to a red oil in vacuo, dissolved in ethyl acetate:acetone (1:1, 5 ml) and added dropwise with stirring to petroleum ether (60°-80°, 50 ml). The deposited solid was collected and dried in a desiccator. The crude product was slurried with ethyl acetate, and the liquid phase was decanted and added dropwise to petroleum ether (60°-80°, 50 ml), yielding the title compound as a colourless solid (150 mg, 40%), λmax (0.25N NaHCO3) 263.5 (ε 15,000) and 281 nm (ε 13,700); νmax (Nujol) 1,799 (β-lactam), 1725 and 1716 (COOH and OCONH2), 1684 and 1538 (CONH) and 1060 and 1050 cm-1 (S→O); τ (Me2SO-d6) values include 0.02 (d, J8Hz, CONH), 4.17(dd, J4 and 8Hz, 7-H), 4.99 (d, J4Hz, 6-H) and 6.09 (s, N-OCH3).

Provenance & Evidence