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

HRID 1982061Notes

Reaction equation

HRID 1982061 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][O:7][N:8]=[C:9]([C:25](OCC)([O:28]CC)[CH2:26][Br:27])[C:10]([NH:12][CH:13]1[C:23](=[O:24])[N:15]2[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]12)=[O:11].O>C(C(C)=O)C(C)C>[CH3:6][O:7][N:8]=[C:9]([C:25](=[O:28])[CH2:26][Br:27])[C:10]([NH:12][CH:13]1[C:23](=[O:24])[N:15]2[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]12)=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric AcidHCID 1317125347-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-cephem-4-carboxylic acid

Product 1

HCID 1317125047-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acidYield 59.4%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

70% Perchloric acid (0.54 ml) was added to a solution of 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 1 g) in methyl isobutyl ketone (4 ml) under ice-cooling, and stirred at the same temperature for 20 minutes. Water (4 ml) was added to the resultant mixture and stirred for 5 minutes. The precipiates were collected by filtration, washed with water and dried over phosphorus pentachloride in vacuo to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 502 mg).

Workup

  1. temperaturecooling
  2. stirringstirred for 5 minutes
  3. filtrationThe precipiates were collected by filtration
  4. washwashed with water
  5. dry with materialdried over phosphorus pentachloride in vacuo

Sources & evidence

ORD record
ord-c273d196746c4085be552c3d2bb6470b
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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