Sulfuric Acid → 7-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-cephem-4-carboxylic acid

HRID 1154837Notes

Reaction equation

HRID 1154837 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][O:9][N:10]=[C:11]([C:28]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])[CH2:29][Br:30])[C:12]([NH:14][CH:15]1[C:26](=[O:27])[N:17]2[CH:18]([C:23]([OH:25])=[O:24])[CH:19](O)[CH2:20][S:21][C@H:16]12)=[O:13].C([O-])(=O)C.[Na+].C([O-])(=O)C.[K+].[Cl-].[Na+].S(=O)(=O)(O)O>O1CCCC1.C(OCC)(=O)C>[CH3:8][O:9][N:10]=[C:11]([C:28]([O:34][CH2:35][CH3:36])([O:31][CH2:32][CH3:33])[CH2:29][Br:30])[C:12]([NH:14][CH:15]1[C:26](=[O:27])[N:17]2[C:18]([C:23]([OH:25])=[O:24])=[CH:19][CH2:20][S:21][C@H:16]12)=[O:13]

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 517045Sodium AcetateHCID 867380937-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125347-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-cephem-4-carboxylic acidYield 121.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
28 °C

Procedure

Acetic anhydride (27.3 ml) was added to a solution of 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 30 g) in dry tetrahydrofuran (300 ml) at room temperature and stirred at 28° C. for 30 minutes. After adding sodium acetate (4.0 g) and potassium acetate (4.7 g) to the solution, the solution was stirred at 28° to 30° C. for 3 hours. The resultant solution was added to a solution of ethyl acetate (300 ml) and a saturated aqueous solution of sodium chloride (300 ml), and adjusted to pH 2.0 with 20% sulfuric acid. After separating the organic layer, the aqueous layer was extracted with ethyl acetate (100 ml) twice. The organic layer and the extract were combined, washed with a saturated aqueous solution of sodium chloride, and then dried over magnesium sulfate. After treating the solution with activated charcoal, the solution was evaporated in vacuo. n-Hexane was added to the residue and decanted to give the oil (35.1 g) of 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer).

Workup

  1. stirringthe solution was stirred at 28° to 30° C. for 3 hours
  2. customAfter separating the organic layer
  3. extractionthe aqueous layer was extracted with ethyl acetate (100 ml) twice
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. additionAfter treating the solution with activated charcoal
  7. customthe solution was evaporated in vacuo
  8. additionn-Hexane was added to the residue
  9. customdecanted

Sources & evidence

ORD record
ord-a473f459fa3e44059b8e065106c4b4bb
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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