Sodium Iodide → HCID 178480376, compound

HRID 1088037Notes

Reaction equation

HRID 1088037 reaction equation
[I-:1].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]1[C:36](=[O:37])[N:13]2[C:14]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:15]([CH2:18]Cl)[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:38][N:39]1[CH:43]=[CH:42][CH:41]=[N:40]1.O1CCCC1>CC(C)=O.O.C(OCC)(=O)C>[I-:1].[C:3]([O:7][C:8]([NH:10][C@@H:11]1[C:36](=[O:37])[N:13]2[C:14]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:15]([CH2:18][N+:40]3[N:39]([CH3:38])[CH:43]=[CH:42][CH:41]=3)[CH2:16][S:17][C@H:12]12)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 702551H-Pyrazole, 1-methyl-HCID 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 178480376HCID 178480376, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium iodide (1.46 g) in acetone (5 ml) was added benzhydryl 7β-tert-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate (5 g) at ambient temperature. The mixture was stirred at the same temperature for 10 minutes and N-methylpyrazole (5 ml) was added thereto. The resultant mixture was stirred at the same temperature for 24 hours and poured into a mixture of tetrahydrofuran (25 ml), ethyl acetate (25 ml) and water (25 ml). The separated organic layer was washed with brine, and dried over magnesium sulfate. The solution was evaporated in vacuo to give benzhydryl 7β-tert-butoxycarbonylamino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (6.45 g), the physical data of which were identical to those of the compound prepared in Preparation 3.

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-cfb8c45eb82741aa8f4a854fddd65083
Source dataset
uspto-grants-1990_10
Patent number
US04960766

Reaction notes

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