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

HRID 1072489Notes

Reaction equation

HRID 1072489 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d080a2ad1b2f4c17aefafbc2835c460e
Source dataset
uspto-grants-2005_06
Patent number
US06911458B2

Reaction notes

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