Potassium Persulfate → HCID 86741374, compound

HRID 1195050Notes

Reaction equation

HRID 1195050 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])(O)=O.[K+].[K+].COC1C=C(OC)C=CC=1C[N:25]1[C@H:28]([CH:29]=[N:30][O:31][CH3:32])[C@H:27]([NH:33][C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[C:26]1=[O:44]>C(#N)C.O.C(OCC)(=O)C>[CH3:32][O:31][N:30]=[CH:29][C@H:28]1[NH:25][C:26](=[O:44])[C@H:27]1[NH:33][C:34]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35]

Participants

7

Reactant 3

HCID 24412Potassium PersulfateHCID 24450Potassium Phosphate, Dibasic2×HCID 86741375HCID 86741375, compound

Product 1

HCID 86741374HCID 86741374, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
78 °C

Procedure

11.9 g (44 mmol) of potassium peroxydisulphate and 9.6 g of dipotassium hydrogen phosphate are dispersed in 110 ml of acetonitrile and 350 ml of water. The mixture is heated to 78° C. and a solution of 11.8 g (27.6 mmol) of benzyl (3S,4S)-1-(2,4-dimethoxybenzyl)-4-[(methoxyimino)methyl]-2-oxo-3-azetidinecarbamate (E/Z mixture) in 300 ml of acetonitrile is added dropwise thereto. The pH of the solution is held at 7 by the addition of dipotassium hydrogen phosphate. After boiling for 6 hours, the mixture is cooled, the aqueous phase is discarded, the organic phase is diluted with ethyl acetate and washed successively with water, aqueous sodium bicarbonate solution and sodium chloride solution. After drying over sodium sulphate, the solvent is removed by evaporation and the crude mixture is chromatographed [230-400 mesh, ethyl acetate/n-hexane (8:2)], there being obtained 1.7 g (27%) of benzyl (3S,4S)-4-[(methoxyimino)methyl]-2-oxo-3-azetidinecarbamate (E/Z mixture); melting point 170°-171° C.

Workup

  1. temperaturethe mixture is cooled
  2. washwashed successively with water, aqueous sodium bicarbonate solution and sodium chloride solution
  3. dry with materialAfter drying over sodium sulphate
  4. customthe solvent is removed by evaporation
  5. customthe crude mixture is chromatographed [230-400 mesh, ethyl acetate/n-hexane (8:2)], there

Sources & evidence

ORD record
ord-7509f13199564786a24656c3a952cbf1
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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