Sodium Hydroxide → HCID 67396046, compound

HRID 1426699Notes

Reaction equation

HRID 1426699 reaction equation
[F:1][C:2]1[C:3]([CH2:26][N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:4][N:5](S(C2C=CC=CC=2)(=O)=O)[C:6]=1[C:7]1[C:8]([C:13]([F:16])([F:15])[F:14])=[N:9][CH:10]=[CH:11][CH:12]=1.[OH-].[Na+]>O1CCCC1.CO>[F:1][C:2]1[C:3]([CH2:26][N:27]([CH3:35])[C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[CH:4][NH:5][C:6]=1[C:7]1[C:8]([C:13]([F:15])([F:16])[F:14])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67395593HCID 67395593, compound

Product 1

HCID 67396046HCID 67396046, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl ({4-fluoro-1-(phenylsulfonyl)-5-[2-(trifluoromethyl)pyridin-3-yl]-1H-pyrrol-3-yl}methyl)methylcarbamate (938 mg) in tetrahydrofuran (4 mL) and methanol (1 mL) was added a 8 mol/L aqueous sodium hydroxide solution (0.6 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1) to give the title compound as a yellow oil (yield 423 mg, 62%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2942764cc30b42b09ab8bd382d41489f
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

Loading…