Ethyl Acetate → 7-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acid

HRID 1982033Notes

Reaction equation

HRID 1982033 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][N:7]=[C:8]([C:24](=[O:26])[CH3:25])[C:9]([NH:11][CH:12]1[C:22](=[O:23])[N:14]2[C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH2:17][S:18][C@H:13]12)=[O:10].[BrH:27].[NH+]1C=CC=CC=1.C(OCC)(=O)C>O1CCCC1.O>[CH3:5][O:6][N:7]=[C:8]([C:24](=[O:26])[CH2:25][Br:27])[C:9]([NH:11][CH:12]1[C:22](=[O:23])[N:14]2[C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH2:17][S:18][C@H:13]12)=[O:10]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 21226041Pyridinium hydrobromideHCID 1317125287-(2-Methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 1317125047-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (120 mg.) was added to a solution of 7-(2-methoxyimino-3-oxobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 50 mg.) in dry tetrahydrofuran (10 ml.). Pridinium hydrobromide perbromide (50 mg.) was added to the solution, and stirred at room temperature for 20 minutes. Ethyl acetate (50 ml.) and water (10 ml.) were added to the resultant solution and the mixture was treated in a similar manner to that of the above Example 10-(8) to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 52.5 mg.)

Workup

  1. additionthe mixture was treated in a similar manner to that of the above Example 10-(8)

Sources & evidence

ORD record
ord-78a632246b0b497396c8cb8386613344
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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