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

HRID 1154818Notes

Reaction equation

HRID 1154818 reaction equation
Cl(O)(=O)(=O)=O.C(OC(NN=[C:13]([CH3:33])[C:14](=[N:30][O:31][CH3:32])[C:15]([NH:17][CH:18]1[C:28](=[O:29])[N:20]2[C:21]([C:25]([OH:27])=[O:26])=[CH:22][CH2:23][S:24][C@H:19]12)=[O:16])=O)C.[OH-:34].[Na+]>>[CH3:32][O:31][N:30]=[C:14]([C:13](=[O:34])[CH3:33])[C:15]([NH:17][CH:18]1[C:28](=[O:29])[N:20]2[C:21]([C:25]([OH:27])=[O:26])=[CH:22][CH2:23][S:24][C@H:19]12)=[O:16]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 1317125327-(3-Ethoxycarbonylhydrazono-2-methoxyiminobutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 1317125287-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid

Procedure

70% Perchloric acid (4.1 ml.) was added to a solution of 7-(3-ethoxycarbonylhydrazono-2-methoxyiminobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 4.1 g.) at room temperature and stirred at the same temperature for 2 hours. After adjusting to pH 2.0 with 1 N sodium hydroxide aq. acetone was evaporated in vacuo from the resultant solution. Ethyl acetate (100 ml.) and a sodium chloride saturated aqueous solution (50 ml.) to the residue and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate (100 ml.) and combined with the ethyl acetate layer. The solution was washed with a sodium chloride saturated aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The residue was pulverized with diisopropyl ether and the precipitates were collected by filtration to give 7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 3.25 g.).

Workup

  1. customwas evaporated in vacuo from the resultant solution
  2. customEthyl acetate (100 ml.) and a sodium chloride saturated aqueous solution (50 ml.) to the residue and the ethyl acetate layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 ml.)
  4. washThe solution was washed with a sodium chloride saturated aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-1c760a32d4b9468fb6bff419e785c9d6
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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