Potassium Persulfate → HCID 70390484, compound

HRID 653292Notes

Reaction equation

HRID 653292 reaction equation
[C:1]([NH:4][CH2:5][C@H:6]1[N:9](CC2C=CC(OC)=CC=2OC)[C:8](=[O:21])[C@H:7]1[NH:22][C:23](=[O:31])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:3])[CH3:2].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P(O)([O-])([O-])=O.[K+].[K+]>O.C(#N)C>[C:1]([NH:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:21])[C@H:7]1[NH:22][C:23](=[O:31])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, DibasicHCID 70390712HCID 70390712, compound

Product 1

HCID 70390484HCID 70390484, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 298 mg of cis-4-acetamidomethyl-1-(2,4-dimethoxybenzyl)-3-phenylacetamido-2-oxoazetidine, 576 mg of potassium persulfate and 183 mg of dipotassium phosphate in 15 ml of water and 15 ml of acetonitrile is heated under reflux for 1.5 hours. The reaction mixture is concentrated in vacuo. The residue is taken up in ethyl acetate and the solution is washed successively with an aqueous sodium hydrogen carbonate solution and an aqueous sodium chloride solution. The ethyl acetate solution is 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-4-acetamidomethyl-3-phenylacetamido-2-oxoazetidine, m.p. 200°-202° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. washthe solution is washed successively with an aqueous sodium hydrogen carbonate solution
  5. dry with materialThe ethyl acetate solution is dried over magnesium sulfate
  6. distillationthe solvent is then distilled off in vacuo
  7. additionEthyl acetate is added to the residue
  8. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-8277827553d346229226ec46ab1f836d
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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