Cesium carbonate → N-Cyclopropyl-4-fluoro-2-(2-oxiranylmethoxy)benzamide

HRID 270064Notes

Reaction equation

HRID 270064 reaction equation
[CH:1]1([NH:4][C:5](=[O:14])[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[OH:13])[CH2:3][CH2:2]1.[O:15]1[CH2:17][C@H:16]1[CH2:18]OS(C1C=CC=C([N+]([O-])=O)C=1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH:1]1([NH:4][C:5](=[O:14])[C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=2[O:13][CH2:18][CH:16]2[CH2:17][O:15]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 68961144N-Cyclopropyl-4-fluoro-2-hydroxybenzamide

Product 1

HCID 45086863N-Cyclopropyl-4-fluoro-2-(2-oxiranylmethoxy)benzamideYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixturte of N-cyclopropyl-4-fluoro-2-hydroxybenzamide (195 mg, 1.0 mmol), (2S)-oxiran-2-ylmethyl3-nitrobenzenesulfonate (259 mg, 1.0 mmol) and Cs2CO3 (390 mg, 1.2 mmol) in DMF (5 mL) was stirred 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 (0-30% ethylacetate in petroleum ether) to give the subtitled compound (150 mg).

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 (0-30% ethylacetate in petroleum ether)

Sources & evidence

ORD record
ord-b7e30bb29ea445ab83e4de635ec2c63e
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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