Diethyl Ether → HCID 131710127, compound

Participants

Reaction Steps

3-Dichloroacetoxymethyl-7β-(2'-thienylacetamido)ceph-3-em-4-carboxylic acid (4.74 g.) was refluxed in ethanol (175 ml.) for 60 minutes; the mixture was filtered and the filtrate evaporated to give an oil. Trituration with ethyl acetate gave a solid (354 mg.), which was discarded. The ethyl acetate solution was extracted with sodium bicarbonate solution; the aqueous layer was then acidified and extracted with ethyl acetate. On drying and evaporation this solution gave a gum (3.34 g.), which was redissolved in hot ethyl acetate. Addition of a fourfold volume of ether gave a solid, which was discarded. The filtrate was concentrated and set aside at 0°; a white solid (548 mg.) crystallised out, m.p. 160°-165° (decomp.), [α]D25 = 157° (c 0.7, tetrahydrofuran) λλmax (NaHCO3 solution) 237nm (ε = 12,800), 260nm (ε = 8,000), νmax (CHBr3) 1770 (β-lactam), 1720 (COOH), 1659 and 1678 cm-1 (CONH). N.M.R. spectrum (D2O, with sodium bicarbonate) -O-CH2.CH3 systems centred at 6.5 and 8.83τ. (Found: C, 50.6; H, 4.8; N, 7.1; S, 16.3. C16H18N2O5S 2 requires C, 50.2; H, 4.7; N, 7.4; S, 16.8%). RF = 1.5 (System C), 1.35 (System B).

Provenance & Evidence