Ethanol → HCID 86624004, compound

HRID 1426792Notes

Reaction equation

HRID 1426792 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:22][N:23](C)[C:24](=O)[O:25][C:26]([CH3:29])(C)C)[C:9]=2[F:32])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:33]([O:36]CC)(=[O:35])[CH3:34].Cl.C([OH:42])C>>[C:26]([OH:25])(=[O:42])/[CH:29]=[CH:34]/[C:33]([OH:36])=[O:35].[Cl:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:22][NH:23][CH3:24])[C:9]=2[F:32])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623991HCID 86623991, compound

Product 1

HCID 86624004HCID 86624004, compound

Procedure

To a solution of tert-butyl {[5-(2-chloropyridin-3-yl)-4-fluoro-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (439 mg) in ethanol (4 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (4 mL), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution 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 free base (267 mg). To a solution of the obtained free base (264 mg) in ethyl acetate (2 mL) was added a solution of fumaric acid (81.1 mg) in ethanol (2 mL), and the mixture was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized from ethanol-water to give the title compound as a white solid (yield 225 mg, 49%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionSaturated aqueous sodium hydrogen carbonate solution 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-6fb3413be7db4667b77a3342c2af8788
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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