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

HRID 1982043Notes

Reaction equation

HRID 1982043 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].CO>C1(OC)C=CC=CC=1.CN(C)C=O.O1CCCC1>[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

7

Reactant 3

HCID 887MethanolHCID 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 85.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 7519AnisoleCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Trifluoroacetic anhydride (1 ml.), anisole (1 drop) and dimethylformamide (1 drop) were added to a solution of 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-hydroxycepham-4-carboxylic acid (syn isomer, 1 g.) in dry tetrahydrofuran (3 ml.) and stirred for 4 hours. After adding methanol (0.3 ml.) into the resultant solution, the solution was stirred for an hour and concentrated in vacuo. The residue was pulverized with diisopropyl ether. The precipitates were collected by filtration and dried over phosphorus pentoxide to give 7-(2-methoxyimino-3-oxo-4-bromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 0.82 g).

Workup

  1. stirringthe solution was stirred for an hour
  2. concentrationconcentrated in vacuo
  3. filtrationThe precipitates were collected by filtration
  4. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-ae9c56e57ad34053be8f39963d272701
Source dataset
uspto-grants-1986_06
Patent number
US04594446

Reaction notes

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