Potassium Persulfate → HCID 10511815, compound

HRID 371229Notes

Reaction equation

HRID 371229 reaction equation
[C:1]1([C@H:7]2[N:10](CC3C=CC(OC)=CC=3OC)[C:9](=[O:22])[C@H:8]2[N:23]=[N+:24]=[N-:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[K+].[K+]>C(#N)C.O>[C:1]1([C@H:7]2[NH:10][C:9](=[O:22])[C@H:8]2[N:23]=[N+:24]=[N-:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, Dibasic2×HCID 86740202HCID 86740202, compound

Product 1

HCID 10511815HCID 10511815, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(±)-(cis)-4-Phenyl-1-(2,4-dimethoxybenzyl)-2-oxo-3-azidoazetidine (737 mg) is dissolved in 25 ml of acetonitrile and heated to 80°-83° C. under nitrogen. To the resulting solution are added over a 1 hour period 943 mg of potassium persulfate and 570 mg of potassium monohydrogen phosphate, both dissolved in 25 ml of water. After the addition, the mixture is further heated at 80°-83° C. for 7 hours. The mixture is cooled and the pH is adjusted to 6-7 by adding solid potassium monohydrogen phosphate. Most of the acetonitrile is removed under reduced pressure and the resulting mixture is extracted with 60 ml of chloroform. The chloroform layer is washed with water (60 ml), dried over anhydrous sodium sulfate and stripped of solvent to give a crude product as an oil. The crude product is chromatographed on 40 g of silica gel eluting with 1:1 petroleum ether-ethyl acetate. The combined fractions yield crystals and the product is recrystallized from petroleum ether-ethyl acetate to give 267 mg of the title compound.

Workup

  1. temperatureheated to 80°-83° C. under nitrogen
  2. additionAfter the addition
  3. temperaturethe mixture is further heated at 80°-83° C. for 7 hours
  4. temperatureThe mixture is cooled
  5. customMost of the acetonitrile is removed under reduced pressure
  6. extractionthe resulting mixture is extracted with 60 ml of chloroform
  7. washThe chloroform layer is washed with water (60 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. customto give a crude product as an oil
  10. customThe crude product is chromatographed on 40 g of silica gel eluting with 1:1 petroleum ether-ethyl acetate
  11. customThe combined fractions yield crystals
  12. customthe product is recrystallized from petroleum ether-ethyl acetate

Sources & evidence

ORD record
ord-98be052e1bf8497e8f865aa9323ca2c9
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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