Hydrochloric Acid → 7-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-cephem-4-carboxylic acid

HRID 1702059Notes

Reaction equation

HRID 1702059 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][O:15][N:16]=[C:17]([C:34]1([O:39][CH2:38][CH2:37][O:36]1)[CH3:35])[C:18]([NH:20][CH:21]1[C:32](=[O:33])[N:23]2[CH:24]([C:29]([OH:31])=[O:30])[CH:25](O)[CH2:26][S:27][C@H:22]12)=[O:19].C(=O)(O)[O-].[Na+].Cl>O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:14][O:15][N:16]=[C:17]([C:34]1([O:39][CH2:38][CH2:37][O:36]1)[CH3:35])[C:18]([NH:20][CH:21]1[C:32](=[O:33])[N:23]2[C:24]([C:29]([OH:31])=[O:30])=[CH:25][CH2:26][S:27][C@H:22]12)=[O:19]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 1317129817-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125317-(2-Methoxyimino-3,3-ethylenedioxybutyramido)-3-cephem-4-carboxylic acidYield 62.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (0.1 ml.) and triethylamine (0.2 ml.) were added to a solution of 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 50 mg.) in dry tetrahydrofuran (5 ml.) and stirred at room temperature for 10 minutes. A sodium bicarbonate aqueous solution (2 ml.) was added to the resultant solution and heated for two minutes. Ethyl acetate and water were added to the solution, acidified with 6 N hydrochloric acid and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The ethyl acetate layer and extract were combined together, washed with water and a sodium chloride aqueous solution in turn and dried over magnesium sulfate. The solution was evaporated in vacuo, and the residue was pulverized with diethyl ether to give 7-(2-methoxyimino-3,3-ethylenedioxybutyramido)-3-cephem-4-carboxylic acid (syn isomer, 30 mg.)

Workup

  1. temperatureheated for two minutes
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. extractionThe ethyl acetate layer and extract
  5. washwashed with water
  6. dry with materiala sodium chloride aqueous solution in turn and dried over magnesium sulfate
  7. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-0369ba83aa0d430299194b87d38cf664
Source dataset
uspto-grants-1983_04
Patent number
US04379922

Reaction notes

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