Potassium Persulfate → HCID 54342386, compound

HRID 1709381Notes

Reaction equation

HRID 1709381 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@@H:12]([C:13]([CH3:20])=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:11](CC2C=CC(OC)=CC=2OC)[C:10]1=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].S([O-])(O)(=O)=O.[K+]>C(#N)C>[CH2:18]([O:17][C:15]([CH:14]=[C:13]([CH:12]1[NH:11][C:10](=[O:32])[CH:9]1[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH3:20])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 24412Potassium PersulfateHCID 516920Potassium bisulfateHCID 131715082HCID 131715082, compound

Product 1

HCID 54342386HCID 54342386, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.0 g (8.9 mmol) of ethyl rac-cis-3-(1-t-butoxyformamido)-1-(2,4-dimethoxybenzyl)-β-methyl-2-oxo-4-azetidineacrylate are dissolved in 300 ml of acetonitrile and the solution is treated at 90°-95° C. with 3.86 g (14.3 mmol) of potassium peroxydisulphate and 2.31 (13.3 mmol) of potassium hydrogen sulphate for 2 hours. The organic solvent is removed by evaporation and the aqueous phase is extracted with chloroform. The combined organic phases are washed with aqueous sodium chloride solution and dried over sodium sulphate. The solution is evaporated and the residue is chromatographed on silica gel using ethyl acetate for the elution. 990 mg (37%) of t-butyl 4-[2-(ethoxycarbonyl)-1-methylvinyl]-2-oxo-3-azetidinecarbamate are obtained.

Workup

  1. customThe organic solvent is removed by evaporation
  2. extractionthe aqueous phase is extracted with chloroform
  3. washThe combined organic phases are washed with aqueous sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customThe solution is evaporated
  6. customthe residue is chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-8bbb2952879b4e37a8b756b010e65f4e
Source dataset
uspto-grants-1990_08
Patent number
US04948898

Reaction notes

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