Ethanol → HCID 66974587, compound

HRID 1962657Notes

Reaction equation

HRID 1962657 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])[N:12]([S:24]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH:11]=1)C)(C)(C)C.[C:34]([O:37]CC)(=[O:36])[CH3:35].Cl.C([OH:43])C>>[C:19]([OH:21])(=[O:43])/[CH:20]=[CH:35]/[C:34]([OH:37])=[O:36].[F:23][C:16]1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=1[C:13]1[N:12]([S:24]([C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)(=[O:26])=[O:25])[CH:11]=[C:10]([CH2:9][NH:7][CH3:6])[CH:14]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974486HCID 66974486, compound

Product 1

HCID 66974587HCID 66974587, compoundYield 78%

Conditions

Temperature
70 °C

Procedure

tert-Butyl{[5-(2-fluoro-5-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (475 mg) was dissolved in ethanol (10 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced pressure, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, added to a solution (13 mL) of fumaric acid (116 mg) in methanol, and the obtained crystals were collected by filtration to give the title compound as colorless crystals (yield 385 mg, 78%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. additionadded to a solution (13 mL) of fumaric acid (116 mg) in methanol
  9. filtrationthe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-23392fd66c8a449b9c11b93560db1b91
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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