Tetrahydrofuran → HCID 67397020, compound

HRID 1426701Notes

Reaction equation

HRID 1426701 reaction equation
[C:1]([C:3]1[C:8]([C:9]2[N:13](S(C3C=CC=CC=3)(=O)=O)[CH:12]=[C:11]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:10]=2[F:33])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].O1CCCC1.[OH-].[Na+]>CO>[C:1]([C:3]1[C:8]([C:9]2[NH:13][CH:12]=[C:11]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28])[C:10]=2[F:33])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67396653HCID 67396653, compound

Product 1

HCID 67397020HCID 67397020, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl {[5-(2-cyanopyridin-3-yl)-4-fluoro-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (5.43 g), tetrahydrofuran (50 mL), and methanol (13 mL) was added a 8 mol/L aqueous sodium hydroxide solution (2 mL) at 0° C., and the mixture was stirred at the same temperature for 30 min. 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=1:1), and further by silica gel column chromatography (eluent: hexane:ethyl acetate=1:1) to give the title compound as a yellow oil (yield 2.18 g, 57%).

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=1:1)

Sources & evidence

ORD record
ord-1706bc51ff834ec98a9d19d7f66f0b93
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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