HCID 70603475, compound → HCID 15742496, compound

Participants

Reaction Steps

A suspension of 3-acetoxymethyl-7β-(2-thienylacetamido)ceph-2-em-4-carboxylic acid (42 g.) in water (400 ml.) was flushed with nitrogen and potassium carbonate (43 g.) added. The mixture was treated with water (200 ml.) to effect complete solution and methanol (50 ml.) added. The solution was stored at 37° for 4.25 hours and then at 22° for 17 hours. The methanol was removed in vacuo and the mixture diluted with water (200 ml.) and stirred with ethyl acetate (800 ml.). The pH of the mixture was adjusted to 2.5 with orthophosphoric acid and the organic layer separated and washed with water and dried. The ethyl acetate was evaporated in vacuo until crystallisation of the product started, and the mixture cooled. Filtration gave the title compound (19.7 g., 52.5%) as fine needles, m.p. 151.5°-152° (decomp), [α]D + 465° (tetrahydrofuran), λmax. 234 nm. (ε 14,400), νmax. 3250 (NH and bonded OH), 2600 and 1725 (CO2H), 1755 (β-lactam) and 1650 and 1520 cm-1 (CONH), τ (D2O-sodium bicarbonate) 2.65 and 3.0 (thienyl, 3-proton complex), 3.7 (C(2) -H), broad s), 4.62 (C(2) -H, d, J 4.5 Hz), 4.74 (C(6) -H, d, J 4.5 Hz), 5.15 (C(4) -H, broad s), 5.8 (CH2OH, broad s) and 6.12(CH2CONH, s). (Found: C, 47.4; H, 4.05; N, 7.65; s 18.0; Calc. for C14H14N2O5S2 : C, 47.5; H, 3.9; N, 7.9; S, 18.1%).

Provenance & Evidence