Isopropanol → HCID 86623992, compound

HRID 1426700Notes

Reaction equation

HRID 1426700 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[N:12](S(C3C=CC=CC=3)(=O)=O)[CH:11]=[C:10]([CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:9]=2[F:32])=[CH:6][CH:5]=[CH:4][N:3]=1.O1CCCC1.CC(O)C.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH2:22][N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[C:9]=2[F:32])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86623991HCID 86623991, compound

Product 1

HCID 86623992HCID 86623992, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl {[5-(2-chloropyridin-3-yl)-4-fluoro-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (5.50 g), tetrahydrofuran (25 mL), 2-propanol (25 mL) and methanol (20 mL) was added a 1 mol/L aqueous sodium hydroxide solution (50 mL), 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=1:1) to give the title compound as a yellow solid (yield 3.59 g, 92%).

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-904c4fcc36e64fe99fee97543439181d
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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