Cesium carbonate → N-(2-{[(2R)-2-Methyloxiranyl]methoxy}phenyl)acetamide

HRID 490318

Reaktionsgleichung

Reaktionsgleichung von HRID 490318
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(S(O[CH2:29][C@@:30]2([CH3:33])[CH2:32][O:31]2)(=O)=O)=CC=1>CN(C=O)C>[CH3:29][C@:30]1([CH2:33][O:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:1](=[O:3])[CH3:2])[CH2:32][O:31]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 119722-AcetamidophenolHCID 10900803[(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonate

Produkt 1

HCID 86597619N-(2-{[(2R)-2-Methyloxiranyl]methoxy}phenyl)acetamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 2-acetamidophenol (90.5 mg, 0.598 mmol) and cesium carbonate (234 mg, 0.718 mmol) was added [(2R)-2-methyloxiranyl]methyl 4-methylbenzene-sulfonate (145 mg, 0.598 mmol) dissolved in DMF (1 ml). The mixture was stirred at room temperature for four hours and then partitioned between ethyl-acetate and water. After extraction the combined organic phases were dried and concentrated in vacuo. The residue was purified on silica (Heptane/EtOAc 3:1-2:1) to give 63 mg (48%) of the title compound.

Aufarbeitung

  1. custompartitioned between ethyl-acetate and water
  2. extractionAfter extraction the combined organic phases
  3. customwere dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica (Heptane/EtOAc 3:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0cac9289f381442fa088d9f34f2fdd15
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528156B2

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