Cesium carbonate → N-(4-Methoxy-2-([(2S)-2-methyloxiran-2-yl]methoxy}phenyl)acetamide

HRID 270076Notes

Reaction equation

HRID 270076 reaction equation
[CH3:1][C@@:2]1([CH2:5]OS(C2C=CC=C([N+]([O-])=O)C=2)(=O)=O)[CH2:4][O:3]1.[OH:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=1[NH:28][C:29](=[O:31])[CH3:30].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:27][O:26][C:24]1[CH:23]=[CH:22][C:21]([NH:28][C:29](=[O:31])[CH3:30])=[C:20]([O:19][CH2:1][C@:2]2([CH3:5])[CH2:4][O:3]2)[CH:25]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 41051392'-Hydroxy-4'-methoxyacetanilideHCID 86597620HCID 86597620, compound

Product 1

HCID 11448100N-(4-Methoxy-2-([(2S)-2-methyloxiran-2-yl]methoxy}phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of [(2S)-2-methyloxiran-2-yl]methyl3-nitrobenzenesulfonate (2.04 g, 7.46 mmol), N-(2-hydroxy-4-methoxyphenyl)acetamide ((1.04 g, 5.74 mmol) and Cs2CO3 (2.80 g, 8.61 mmol) in DMF (12 mL) was kept on stirring at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel flash chromatography (ethyl acetate:hexane 1:1) to give the subtitled compound (1.19 g).

Workup

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

Sources & evidence

ORD record
ord-d0862cfd5414480b919ba963b7446835
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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