Potassium Persulfate → HCID 54087854, compound

HRID 260505Notes

Reaction equation

HRID 260505 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH:9]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:8]([C@H:20]([OH:22])[CH3:21])[C:7]1=[O:23].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O>[OH:22][C@@H:20]([CH:8]1[CH:9]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[NH:6][C:7]1=[O:23])[CH3:21]

Participants

6

Reactant 3

HCID 24412Potassium PersulfateHCID 62657Potassium Phosphate, TribasicHCID 54296507HCID 54296507, compound

Product 1

HCID 54087854HCID 54087854, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

3(a) 14 g of benzyl 1-(2,4-dimethoxybenzyl)-3-[(R)-1-hydroxyethyl]-2-oxoazetidine-4-carboxylate [which had been synthesized according to a procedure similar to that described in Tetrahedron 46, 1795 (1984)] were dissolved in a mixture of 420 ml of acetonitrile and 420 ml of water. 66.1 g of potassium persulfate and 23.3 g of dibasic potassium phosphate were added to the solution, and the mixture was stirred at 70° C. for 60 minutes. At the end of this time, insoluble materials were filtered off, and the filtrate was concentrated by evaporation under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and freed from the solvent by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel to afford 6.1 g of benzyl 3-[(R)-1-hydroxyethyl]-2-oxoazetidine-4-carboxylate.

Workup

  1. filtrationAt the end of this time, insoluble materials were filtered off
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customfreed from the solvent by evaporation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-a77e8eff88624868b57ebfcf085f4d1d
Source dataset
uspto-grants-1996_06
Patent number
US05527905

Reaction notes

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