Perchloric Acid → 7-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

HRID 1154839Notes

Reaction equation

HRID 1154839 reaction equation
Cl(O)(=O)(=O)=O.[CH3:6][O:7][N:8]=[C:9]([C:26](OCC)([O:29]CC)[CH2:27][Br:28])[C:10]([NH:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[CH:17]([OH:20])[CH2:18][S:19][C@H:14]12)=[O:11]>CC(C)=O>[CH3:6][O:7][N:8]=[C:9]([C:26](=[O:29])[CH2:27][Br:28])[C:10]([NH:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[CH:17]([OH:20])[CH2:18][S:19][C@H:14]12)=[O:11]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 867380937-(2-Methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 867380917-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acidYield 43.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

70% Perchloric acid (3.4 ml) was added to a solution of 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 5.0 g) in acetone (40 ml) under ice-cooling and stirred at the same temperature for an hour. The precipitates were collected by filtration, washed with acetone (5 ml) twice and dried to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 1.85 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with acetone (5 ml) twice
  4. customdried

Sources & evidence

ORD record
ord-c3290fc088ff4c7bad4772c07eb72497
Source dataset
uspto-grants-1981_11
Patent number
US04298529

Reaction notes

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