Acetone → HCID 131710756, compound

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A solution of sodium 3-acetoxymethyl-7β-[2-hydroxyimino-2-(thien-2-yl)acetamido]ceph-3-em-4-carboxylate (syn-isomer) (2.0 g) in water (160 ml) was warned to 37° and defatted wheat germ (15 g.) was added. The mixture was stirred at 37° for 4 hours, the pH being kept between 6.5 and 6.9 by the addition of 2N sodium hydroxide solution (total 2.3 ml). The mixture was poured into acetone (200 ml) and then filtered through kieselguhr. Acetone was removed under reduced pressure and the aqueous solution was again filtered through kieselguhr, washed with ethyl acetate, then covered with ethyl acetate and taken to ph 2.7 by the careful addition of concentrated hydrochloric acid. The layers were separated and the aqueous layer was re-extracted with ethyl acetate. The combined extracts were washed with water and the pH was taken to 7.0 by the addition of 2N-sodium hydroxide. The organic layer was further extracted with water and the combined aqueous solution was washed with ethyl acetate and ether, degassed and lyophilised to give the title oxime as a brown solid (1.43 g; 79%), [α]D + 76° (c 0.46, DMSO), λmax. (pH 6 phosphate) 261.5 nm (ε 10,600), λinflex. 284 nm (ε 6,500), νmax. (Nujol) 1760 (β-lactam), 1560 (CO-2), 1650 and 1520 cm-1 (COHN), τ (D2O) values include 2.41, 2.63 and 2.83 (doublet, doublet and triplet respectively, J 4 Hz; thienyl protons)

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