Acetone → HCID 131710756, compound

HRID 2398138Notes

Reaction equation

HRID 2398138 reaction equation
C([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:27])[C:19](=[N:25][OH:26])[C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=O)C.[Na+:29].[OH-].[Na+].CC(C)=O>O>[OH:26][N:25]=[C:19]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)[C:18]([NH:17][C@@H:16]1[C:15](=[O:28])[N:10]2[C:11]([C:12]([O-:14])=[O:13])=[C:6]([CH2:5][OH:4])[CH2:7][S:8][C@H:9]12)=[O:27].[Na+:29]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 131710758HCID 131710758, compound

Product 1

HCID 131710756HCID 131710756, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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)

Workup

  1. customwas warned to 37°
  2. additionwas added
  3. filtrationfiltered through kieselguhr
  4. customAcetone was removed under reduced pressure
  5. filtrationthe aqueous solution was again filtered through kieselguhr
  6. washwashed with ethyl acetate
  7. additiontaken to ph 2.7 by the careful addition of concentrated hydrochloric acid
  8. customThe layers were separated
  9. extractionthe aqueous layer was re-extracted with ethyl acetate
  10. washThe combined extracts were washed with water
  11. additionthe pH was taken to 7.0 by the addition of 2N-sodium hydroxide
  12. extractionThe organic layer was further extracted with water
  13. washthe combined aqueous solution was washed with ethyl acetate and ether
  14. customdegassed

Sources & evidence

ORD record
ord-5a641f95df3e4d35ad7691a18ce77c7a
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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