Water → 7-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid

HRID 1982039Notes

Reaction equation

HRID 1982039 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][O:7][N:8]=[C:9]([C:25]1(OCC[O:27]1)[CH3:26])[C:10]([NH:12][CH:13]1[C:23](=[O:24])[N:15]2[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]12)=[O:11].O>CC(C)=O>[CH3:6][O:7][N:8]=[C:9]([C:25](=[O:27])[CH3:26])[C:10]([NH:12][CH:13]1[C:23](=[O:24])[N:15]2[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]12)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric AcidHCID 1317125317-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 1317125287-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acidYield 59.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

70% Perchloric acid (1.09 ml.) was added to a solution of 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-cephem-4-carboxylic acid (syn isomer, 10.9 g.) in acetone (270 ml.) and stirred at room temperature for 3 hours. Water (150 ml.) was added to the resultant solution and acetone was removed in vacuo. Ethyl acetate (300 ml.) was added to the residue and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate (400 ml.) and then the ethyl acetate extract was combined with ethyl acetate layer. The organic solution was washed with a sodium chloride saturated aqueous solution, allowed to stand in refrigerator overnight and dried over magnesium sulfate. The solution was concentrated in vacuo and the residue was pulverized with diisopropyl ether to give 7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 5.75 g.).

Workup

  1. customwas removed in vacuo
  2. additionEthyl acetate (300 ml.) was added to the residue
  3. customthe ethyl acetate layer was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (400 ml.)
  5. extractionthe ethyl acetate extract
  6. washThe organic solution was washed with a sodium chloride saturated aqueous solution
  7. customto stand in refrigerator overnight
  8. dry with materialdried over magnesium sulfate
  9. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2bc7958dd03d404182374a7de2f4f0e0
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

Loading…