Sodium Acetate Trihydrate → 7-{2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido}-3-methoxy-3-cephem-4-carboxylic acid

HRID 434940Notes

Reaction equation

HRID 434940 reaction equation
FC(F)(F)C([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:29][O:30][CH3:31])[C:12]([NH:14][CH:15]2[C:27](=[O:28])[N:17]3[C:18]([C:24]([OH:26])=[O:25])=[C:19]([O:22][CH3:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1)=O.O.O.O.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.O1CCCC1.O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:29][O:30][CH3:31])[C:12]([NH:14][CH:15]2[C:27](=[O:28])[N:17]3[C:18]([C:24]([OH:26])=[O:25])=[C:19]([O:22][CH3:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1

Participants

6

Reactant 2

HCID 23665404Sodium Acetate TrihydrateHCID 1317124397-[2-{2-(2,2,2-Trifluoroacetamido)-4-thiazolyl}--methoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acid

Product 1

HCID 1317124407-{2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido}-3-methoxy-3-cephem-4-carboxylic acidYield 89.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-[2-{2-(2,2,2-trifluoroacetamido)-4-thiazolyl}-2-methoxyiminoacetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer, 0.55 g.) and sodium acetate trihydrate (1,76 g.) in ethyl acetate (3 ml.), tetrahydrofuran (3 ml.) and water (5.5 ml.) was stirred at room temperature overnight. The aqueous layer was separated from the resultant mixture, washed with dichloromethane, and then evaporated under reduced pressure to remove the organic solvent. The aqueous solution was adjusted to pH 4.2 under ice-cooling, and subjected to column chromatography on Diaion HP-20 resin (Trade mark: manufactured by Mitsubishi Chemical Industries Ltd., 15 ml.). After washing the column with water, the object compound was eluted with 20% aqueous isopropyl alcohol. The eluate was concentrated under reduced pressure and the residue was lyophilized to give 7-{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido}-3-methoxy-3-cephem-4-carboxylic acid (syn isomer 0.4 g.), m.p. 185° to 190° C. (dec.).

Workup

  1. customThe aqueous layer was separated from the resultant mixture
  2. washwashed with dichloromethane
  3. customevaporated under reduced pressure
  4. customto remove the organic solvent
  5. temperaturecooling
  6. washAfter washing the column with water
  7. washthe object compound was eluted with 20% aqueous isopropyl alcohol
  8. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae947efdee89471daef297ba0a38a102
Source dataset
uspto-grants-1983_08
Patent number
US04399133

Reaction notes

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