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

HRID 1905206Notes

Reaction equation

HRID 1905206 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-1d9409738b894b738a3118f65c179b65
Source dataset
uspto-grants-1989_06
Patent number
US04841062

Reaction notes

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