Hydrogen Bromide → 7-(2-Methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acid

HRID 1164263Notes

Reaction equation

HRID 1164263 reaction equation
C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].C([O-])(=O)C.[K+].[CH3:18][O:19][N:20]=[C:21]([C:38](=[O:42])[CH:39]([Br:41])[Br:40])[C:22]([NH:24][CH:25]1[C:36](=[O:37])[N:27]2[CH:28]([C:33]([OH:35])=[O:34])[CH:29](O)[CH2:30][S:31][C@H:26]12)=[O:23].Br>O1CCCC1>[CH3:18][O:19][N:20]=[C:21]([C:38](=[O:42])[CH:39]([Br:40])[Br:41])[C:22]([NH:24][CH:25]1[C:36](=[O:37])[N:27]2[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH2:30][S:31][C@H:26]12)=[O:23]

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 7918Acetic AnhydrideHCID 517044Potassium AcetateHCID 517045Sodium AcetateHCID 867387467-(2-Methoxyimino-3-oxo-4,4-dibromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317129327-(2-Methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acidYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Acetic anhydride (5 ml), sodium acetate (0.61 g) and potassium acetate (0.73 g) were added a solution of 7-(2-methoxyimino-3-oxo-4,4-dibromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 5 g) in dry tetrahydrofuran (50 ml), and stirred at 28° to 29° C. for 4 hours. After hydrogen bromide (5 ml) was added to the resultant solution, tetrahydrofuran was removed under reduced pressure therefrom. To the residue was added water (30 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with water and 30% aqueous solution of sodium bromide in turn, and then dried over anhydrous magnesium sulfate. The solution was treated with activated charcoal, and concentrated under reduced pressure, and then the residue was pulverized with diisopropyl ether. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-(2-methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 2.85 g).

Workup

  1. customwas removed under reduced pressure
  2. additionTo the residue was added water (30 ml) and ethyl acetate (100 ml)
  3. customThe organic layer was separated
  4. washwashed with water and 30% aqueous solution of sodium bromide in turn
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionThe solution was treated with activated charcoal
  7. concentrationconcentrated under reduced pressure
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-7236957926244c41bef7965f1710ff64
Source dataset
uspto-grants-1983_01
Patent number
US04368325

Reaction notes

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