Hydrogen Peroxide → HCID 54126864, compound

HRID 2231516Notes

Reaction equation

HRID 2231516 reaction equation
[CH2:1]([S:3][C@@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2].OO.O.C(OCC)(=[O:25])C>CO>[CH2:1]([S:3]([C@@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:25])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 8857Ethyl AcetateHCID 54565496HCID 54565496, compound

Product 1

HCID 54126864HCID 54126864, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.224 g of (3R,4S)-4-ethylthio-3-phenoxyacetamido-2-oxoazetidine in 3 ml of methanol is added 0.16 ml of 30% aqueous hydrogen peroxide and the mixture is stirred at room temperature for 4 hours. Then, 0.1 ml of 30% aqueous hydrogen peroxide is added, and the mixture is further stirred for 4 hours, followed by addition of 10 ml of water Extraction is carried out with ethyl acetate. The organic layer is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 0.20 g of (3R,4S)-4-ethylsulfinyl-3-phenoxyacetamido-2-oxoazetidine.

Workup

  1. stirringthe mixture is further stirred for 4 hours
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c65b18710d347dfbfa1e82aa0226fb7
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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