Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methoxy-1-pyridiniomethyl)-3-cephem-4-carboxylate

HRID 34501

Reaction equation

HRID 34501 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:28][O:29][CH:30]([F:32])[F:31])[C:8]([NH:10][CH:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([OH:25])=[O:24])=[C:15]([CH2:18]OC(=O)C)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1.[I-].[Na+].Cl>O.C(#N)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:28][O:29][CH:30]([F:32])[F:31])[C:8]([NH:10][CH:11]2[C:26](=[O:27])[N:13]3[C:14]([C:23]([O-:25])=[O:24])=[C:15]([CH2:18][N+:38]4[CH:39]=[CH:40][C:35]([O:34][CH3:33])=[CH:36][CH:37]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 692784-MethoxypyridineHCID 1317156807-[2-(2-Aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317156787-[2-(2-Aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methoxy-1-pyridiniomethyl)-3-cephem-4-carboxylateYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid (syn isomer) (3.0 g), 4-methoxypyridine (4.0 g), sodium iodide (8.0 g), acetonitrile (4.0 ml) and water (1.0 ml) was heated for 2.0 hours at 65° to 68° C., and then water (100 ml) was added thereto. The mixture was adjusted to pH 3.0 with 1N-hydrogen chloride and the resultant precipitates were filtered off. The aqueous layer was subjected to column chromatography on macroporus nonionic adsorption resin "Diaion HP-20" and the elution was carried out with 30% aqueous methanol. The fractions containing the object compound were collected, concentrated in vacuo and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(4-methoxy-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.43 g).

Workup

  1. temperaturewas heated for 2.0 hours at 65° to 68° C.
  2. customthe resultant precipitates
  3. filtrationwere filtered off
  4. washthe elution
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-350e066b5c254a018bc79404d8d526a8
Source dataset
uspto-grants-1988_08
Patent number
US04761410

Linked notes

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