Potassium Persulfate → HCID 70391162, compound

HRID 621028Notes

Reaction equation

HRID 621028 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[N:8](CC2C=CC(OC)=CC=2OC)[C:7](=[O:20])[C@H:6]1[NH:21][C:22](=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:4].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P(O)([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:20])[C@H:6]1[NH:21][C:22](=[O:30])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:4]

Participants

6

Reactant 3

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, DibasicHCID 70390633HCID 70390633, compound

Product 1

HCID 70391162HCID 70391162, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 412 mg of cis-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester, 810 mg of potassium persulfate and 261 mg of dipotassium phosphate in 20 ml of acetonitrile and 20 ml of water is heated under reflux for one hour. The reaction mixture is concentrated in vacuo and the residue is dissolved in ethyl acetate, and washed successively with an aqueous 5% sodium hydrogen carbonate solution and an aqueous sodium chloride solution, and dried over magnesium sulfate, and the solvent is then distilled off in vacuo. Ethyl acetate is added to the residue and the precipitated crystals are collected by filtration to give cis-3-phenylacetamido-2-oxoazetidine-4-carboxylic acid methyl ester, m.p. 176°-180° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for one hour
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. washwashed successively with an aqueous 5% sodium hydrogen carbonate solution
  6. dry with materialan aqueous sodium chloride solution, and dried over magnesium sulfate
  7. distillationthe solvent is then distilled off in vacuo
  8. additionEthyl acetate is added to the residue
  9. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-491e16f0de6148c68df414a10147bcd0
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

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