Cesium carbonate → N-{2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270054Notes

Reaction equation

HRID 270054 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:11])[CH3:10].[O:12]1[CH2:14][C@H:13]1[CH2:15]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[O:12]1[CH2:14][C@H:13]1[CH2:15][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 119722-AcetamidophenolHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 6933328N-{2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetamideYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(2-hydroxyphenyl)acetamide (1.51 g, 10 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (2.59 g, 10 mmol) and cesium carbonate (Cs2CO3) (3.9 g, 12 mmol) in dimethylformamide (DMF) (30 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered, concentrated and the residue was purified by silica gel flash chromatography to give the subtitled compound (1.34 g).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-438c1343033a4e1aadbcfb9772f1c70f
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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