Methanol → HCID 67397796, compound

HRID 1426778Notes

Reaction equation

HRID 1426778 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:24][N:25](C)[C:26](=O)[O:27][C:28]([CH3:31])(C)C)[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[OH:35].[C:36]([O:39]CC)(=[O:38])[CH3:37].Cl>C(OCC)(=O)C>[C:28]([OH:35])(=[O:27])/[CH:31]=[CH:37]/[C:36]([OH:39])=[O:38].[F:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)(=[O:14])=[O:15])[CH:11]=[C:10]([CH2:24][NH:25][CH3:26])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623986HCID 86623986, compound

Product 1

HCID 67397796HCID 67397796, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl ({5-(2-fluoropyridin-3-yl)-1-[(3-methoxyphenyl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate (303 mg) was dissolved in ethyl acetate (1 mL) and methanol (1 mL) and 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) were added. The mixture was stirred at room temperature for 2 hr, and 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 was washed with 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→1:9) to give the title compound as a free base (149 mg). A solution of the obtained free base (149 mg) in ethyl acetate (2 mL) was added to a solution of fumaric acid (46 mg) in methanol (2 mL), and the mixture was concentrated under reduced pressure. The obtained crystals were recrystallized from a mixed solvent of ethanol-water=9:1 to give the title compound as colorless crystals (yield 138 mg, 44%).

Workup

  1. concentrationconcentrated 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 was washed with 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→1:9)

Sources & evidence

ORD record
ord-a06bfaee2d1e4feea1a4efdb513cd274
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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