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

HRID 1702088Notes

Reaction equation

HRID 1702088 reaction equation
Cl.[CH3:2][O:3][N:4]=[C:5]([C:22](OCC)([O:25]CC)[CH2:23][Br:24])[C:6]([NH:8][CH:9]1[C:20](=[O:21])[N:11]2[CH:12]([C:17]([OH:19])=[O:18])[CH:13]([OH:16])[CH2:14][S:15][C@H:10]12)=[O:7]>C(Cl)Cl>[CH3:2][O:3][N:4]=[C:5]([C:22](=[O:25])[CH2:23][Br:24])[C:6]([NH:8][CH:9]1[C:20](=[O:21])[N:11]2[CH:12]([C:17]([OH:19])=[O:18])[CH:13]([OH:16])[CH2:14][S:15][C@H:10]12)=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric 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 121.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6 N Hydrochloric acid (2 ml) was added to a solution of 7-(2-methoxyimino-3,3-diethoxy-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 500 mg) in methylene chloride (5 ml) under ice-cooling and stirred at room temperature for 70 minutes. The precipitates were collected by filtration, washed with a saturated aqueous solution of sodium chloride (5 ml) and methylene chloride (1 ml) successively, and dried over phosphorus pentachloride to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 517 mg), purity: 57.8%.

Workup

  1. temperaturecooling
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with a saturated aqueous solution of sodium chloride (5 ml) and methylene chloride (1 ml) successively
  4. dry with materialdried over phosphorus pentachloride

Sources & evidence

ORD record
ord-9b490d930269487698d38ef4e75747cb
Source dataset
uspto-grants-1983_04
Patent number
US04379922

Reaction notes

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