Water → HCID 19710957, compound

HRID 724786Notes

Reaction equation

HRID 724786 reaction equation
[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH:12]([NH:15][C:16](=[O:22])[C:17]([Cl:21])([CH3:20])[CH2:18]Cl)[C:11]2=[O:23])[CH:7]=[CH:8][CH:9]=1.[F-].[Cs+].O>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[F:1][C:2]([F:25])([F:24])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:18][C:17]([Cl:21])([CH3:20])[C:16]3=[O:22])[C:11]2=[O:23])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25953Cesium fluorideHCID 19710975HCID 19710975, compound

Product 1

HCID 19710957HCID 19710957, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-(3-trifluoromethoxyphenyl)-3-(2,3-dichloro-2-methylpropanoyl)amino-2-pyrrolidinone (0.82 g) in THF (10 ml) was treated with caesium fluoride (1.29 g) followed by benzyltriethyl ammonium chloride (0.09 g). The mixture was heated under reflux, cooled and poured into water. The resultant mixture was extracted with chloroform (x3) and the combined extracts dried (Na2SO4). Evaporation of the solvent under reduced pressure left an oil which was purified by chromatography on silica-gel, eluting with ethyl acetate/hexane mixtures, to give the title compound as a mixture of diastereomers:

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. extractionThe resultant mixture was extracted with chloroform (x3)
  5. dry with materialthe combined extracts dried (Na2SO4)
  6. customEvaporation of the solvent under reduced pressure
  7. waitleft an oil which
  8. customwas purified by chromatography on silica-gel
  9. washeluting with ethyl acetate/hexane mixtures

Sources & evidence

ORD record
ord-daed483a4fd14db7b838902888b633ec
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

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