Cesium carbonate → N-{4-Fluoro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

HRID 270056Notes

Reaction equation

HRID 270056 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[CH:3]=1.[O:13]1[CH2:15][C@H:14]1[CH2:16]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH2:16][C@@H:14]2[CH2:15][O:13]2)[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 177738N-(4-fluoro-2-hydroxyphenyl)acetamide

Product 1

HCID 20806548N-{4-Fluoro-2-[(2S)-oxiran-2-ylmethoxy]phenyl}acetamideYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-fluoro-2-hydroxyphenyl)acetamide (1.69 g, 10.0 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (2.59 g, 10.0 mmol) and Cs2CO3 (4.87 g, 15.0 mmol) in DMF (15 mL) was stirred at room temperature for 2 h. The reaction mixture was partitioned between ethylacetate and H2O. The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica gel flash chromatography to give the subtitled compound (1.35 g).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate 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-c2a74e928c0541fabba85367338fbe14
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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