Sodium Iodide → HCID 70194500, compound

HRID 744870Notes

Reaction equation

HRID 744870 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:15]([CH2:19]Br)[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C([O-])=[O:33].[NH4+].[I-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:15]([CH2:19][OH:33])[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 5238Sodium Iodide2×HCID 8857Ethyl AcetateHCID 2724268Ammonium trifluoroacetate2×HCID 70195797HCID 70195797, compound

Product 1

HCID 70194500HCID 70194500, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 7-phenylacetamido-3-bromomethyl-3-cephem-4-carboxylate-1-oxide (76.1 g; 0.158 mol) in N,N-dimethylformamide (350 ml), ammonium trifluoroacetate (41.3 g; 0.316 mol) and sodium iodide (23.6 g; 0.158 mol) were added, followed by stirring at room temperature. The reaction mixture was added with ammonium trifluoroacetate (10.3 g; 0.079 mol) upon an elapsed time of 4 hours and 35 minutes from the initiation of the stirring and then with sodium iodide (11.8 g, 0.079 mol) upon an elapsed time of 8 hours and 5 minutes after the initiation of the stirring. Stirring was continued at room temperature for 24 hours and 25 minutes in total. The reaction mixture was poured into a mixture of ethyl acetate, and water and the ethyl acetate layer was collected. The water layer was extracted twice with ethyl acetate. Ethyl acetate layers were combined together, successively washed with water and saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. The solvent was then distilled off under reduced pressure, whereby tert-butyl 7-phenylacetamido-3-hydroxymethyl-3-cephem-4-carboxylate-1-oxide was obtained (yield: 63.5 g; 6.1%).

Workup

  1. stirringStirring
  2. customthe ethyl acetate layer was collected
  3. extractionThe water layer was extracted twice with ethyl acetate
  4. washsuccessively washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-0edf3332e279457abd4ecd6ea6b01e19
Source dataset
uspto-grants-1996_09
Patent number
US05559225

Reaction notes

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