Water → HCID 19710973, compound

HRID 724785Notes

Reaction equation

HRID 724785 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]([CH3:21])([CH3:20])[CH2:18]Cl)[C:11]2=[O:23])[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].O>C1COCC1>[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]([CH3:21])([CH3:20])[C:16]3=[O:22])[C:11]2=[O:23])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 19710969HCID 19710969, compound

Product 1

HCID 19710973HCID 19710973, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-(3-trifluoromethoxyphenyl)-3-(3-chloro-2,2-dimethylpropanoyl)amino-2-pyrrolidinone (0.31 g) in THF (5 ml) was treated with a 60% dispersion of sodium hydroxide in oil (0.036 g). Once the effervescence had ceased, the yellow mixture was stirred for 5 min then poured into water. The mixture was extracted with dichloromethane (x2), the combined extracts were washed with brine and dried (MgSO4). 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 pale tan crystalline solid (0.20 g).

Workup

  1. extractionThe mixture was extracted with dichloromethane (x2)
  2. washthe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the solvent under reduced pressure
  5. waitleft an oil, which
  6. customwas purified by chromatography on silica-gel
  7. washeluting with ethyl acetate/hexane mixtures

Sources & evidence

ORD record
ord-84abde7651ed43478869b24673cdcd5c
Source dataset
uspto-grants-1998_01
Patent number
US05705456

Reaction notes

Loading…