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

HRID 1982051Notes

Reaction equation

HRID 1982051 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][O:15][N:16]=[C:17]([C:34](=[O:37])[CH2:35][Br:36])[C:18]([NH:20][CH:21]1[C:32](=[O:33])[N:23]2[CH:24]([C:29]([OH:31])=[O:30])[CH:25](O)[CH2:26][S:27][C@H:22]12)=[O:19].C(N(CC)CC)C.Cl>C(OCC)(=O)C>[CH3:14][O:15][N:16]=[C:17]([C:34](=[O:37])[CH2:35][Br:36])[C:18]([NH:20][CH:21]1[C:32](=[O:33])[N:23]2[C:24]([C:29]([OH:31])=[O:30])=[CH:25][CH2:26][S:27][C@H:22]12)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 867380917-(2-Methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid

Product 1

HCID 1317125047-(2-Methoxyimino-3-oxo-bromobutyramido)-3-cephem-4-carboxylic acidYield 99.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Trifluoroacetic anhydride (0.5 ml.) was added to a solution of 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 180 mg.) in dry tetrafuran (10 ml.) and stirred at room temperature for 10 minutes. Triethylamine (0.2 ml.) was added to the resultant solution and stirred at room temperature for 10 minutes. Ethyl acetate was added to the solution and adjusted to pH 2.0 with 6N hydrochloric acid. The solution was washed with water and a sodium chloride saturated aqueous solution successively and dried over magnesium sulfate. After the solution was concentrated in vacuo, the residue was pulverized with diisopropyl ether to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 171.5 mg.).

Workup

  1. stirringstirred at room temperature for 10 minutes
  2. washThe solution was washed with water
  3. dry with materiala sodium chloride saturated aqueous solution successively and dried over magnesium sulfate
  4. concentrationAfter the solution was concentrated in vacuo

Sources & evidence

ORD record
ord-c92c2367f1224d4b81c3df83c99ac2ef
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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