Hydrochloric Acid → 7-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acid

HRID 1154824Notes

Reaction equation

HRID 1154824 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:21](=[O:24])[CH2:22][Br:23])[C:5]([NH:7][CH:8]1[C:19](=[O:20])[N:10]2[CH:11]([C:16]([OH:18])=[O:17])[CH:12](O)[CH2:13][S:14][C@H:9]12)=[O:6].C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].Cl>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:21](=[O:24])[CH2:22][Br:23])[C:5]([NH:7][CH:8]1[C:19](=[O:20])[N:10]2[C:11]([C:16]([OH:18])=[O:17])=[CH:12][CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 867380917-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125047-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acidYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 10 g.) was added to dry tetrahydrofuran (100 ml.) at 30° C. To the solution was added acetic anhydride (10 ml.) and stirred at the same temperature for 30 minutes. Sodium acetate (3 g.) was added to the solution and stirred at 30° C. for 4 hours. 6 N Hydrochloric acid (10 ml) was dropwise added to the reaction mixture under ice-cooling and the solvent was evaporated in vacuo below 30° C. After adding water into the residue, the mixture was stirred at 20° to 25° C. for 30 minutes. The precipitates were collected by filtration, washed with water and dried to give 7-(2-methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 7 g.).

Workup

  1. stirringstirred at 30° C. for 4 hours
  2. temperaturecooling
  3. customthe solvent was evaporated in vacuo below 30° C
  4. additionAfter adding water into the residue
  5. stirringthe mixture was stirred at 20° to 25° C. for 30 minutes
  6. filtrationThe precipitates were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5121860ed1fd4e7390fc3f92b4ad5bb5
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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