Sodium Iodide → HCID 70391052, compound

HRID 2231569Notes

Reaction equation

HRID 2231569 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)[C@H:8]([NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]1=[O:32].[I-:39].[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:4]=1[CH2:5][N:6]1[C@H:9]([CH2:10][I:39])[C@H:8]([NH:22][C:23](=[O:31])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]1=[O:32]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 86740463HCID 86740463, compound

Product 1

HCID 70391052HCID 70391052, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 70 ml of acetone are added 2.27 g of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-4-(p-toluenesulfonyloxymethyl)-2-oxoazetidine and 4.95 g of sodium iodide, and the mixture is heated under reflux for 6 hours with stirring, and then concentrated in vacuo. To the residue are added methylene chloride and water to dissolve it, and the methylene chloride layer is separated and washed successively with an aqueous sodium thiosulfate solution and an aqueous sodium chloride solution. The methylene chloride layer is then dried over magnesium sulfate and the solvent is distilled off in vacuo. Ethyl acetate is added to the residue and the precipitated crystals are collected by filtration to give cis-1-(2,4-dimethoxybenzyl)-4-iodomethyl-3-phenylacetamido-2-oxoazetidine, m.p. 181°-182° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 6 hours
  3. concentrationconcentrated in vacuo
  4. additionTo the residue are added methylene chloride and water
  5. dissolutionto dissolve it
  6. customthe methylene chloride layer is separated
  7. washwashed successively with an aqueous sodium thiosulfate solution
  8. dry with materialThe methylene chloride layer is then dried over magnesium sulfate
  9. distillationthe solvent is distilled off in vacuo
  10. additionEthyl acetate is added to the residue
  11. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-404e6f0a28ce4e98b5b072f63c781263
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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