Water → Benzhydryl 7beta-tert-butoxycarbonylamino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide

HRID 1031196Notes

Reaction equation

HRID 1031196 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16]Cl)[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-:36].[Na+].[CH:38]([NH:40][C:41]1[N:45]([CH3:46])[N:44]=[CH:43][CH:42]=1)=[O:39].O>CC(C)=O.C(OCC)(=O)C>[I-:36].[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][N+:44]3[N:45]([CH3:46])[C:41]([NH:40][CH:38]=[O:39])=[CH:42][CH:43]=3)[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 27558695-Formamido-1-methylpyrazoleHCID 11756232(6R,7R)-Benzhydryl 7-((tert-butoxycarbonyl)amino)-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 10628738Benzhydryl 7beta-tert-butoxycarbonylamino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodideYield 98.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of benzhydryl 7β-tert-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate (15 g) and sodium iodide (4.37 g) in acetone (15 ml) was added 5-formamido-1-methylpyrazole (15 g) at ambient temperature. After being stirred for 40 hours at the same temperature, the mixture was poured into a mixture of water and ethyl acetate. The organic layer was separated and washed with water, aqueous sodium chloride solution, and dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7β-tert-butoxycarbonylamino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (20.95 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water, aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-4caf531abebe4a639379e44aa40b273a
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

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