Ethyl Acetate → HCID 66974457, compound

HRID 1962658Notes

Reaction equation

HRID 1962658 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[N:12]([S:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:11]=1)C)(C)(C)C.[C:32]([O:35]CC)(=[O:34])[CH3:33].Cl.[C:39]([O:42]CC)(=[O:41])[CH3:40]>CO>[C:39]([OH:42])(=[O:41])/[CH:40]=[CH:33]/[C:32]([OH:35])=[O:34].[F:21][C:16]1[C:15]([C:13]2[N:12]([S:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)(=[O:23])=[O:24])[CH:11]=[C:10]([CH2:9][NH:7][CH3:6])[CH:14]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974416HCID 66974416, compound

Product 1

HCID 66974457HCID 66974457, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl{[5-(2-fluoropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (2.48 g) in ethyl acetate (10 mL) and methanol (10 mL) was added a 4 mol/L hydrogen chloride-ethyl acetate solution (20 mL) at room temperature. After stirring for 5 hr, the mixture was concentrated under reduced pressure. The residue was basified with a saturated aqueous sodium hydrogencarbonate solution and 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 a free salt of the title compound as a pale-yellow oil. The obtained free salt was dissolved in ethyl acetate (10 mL) and added to a solution of (10 mL) fumaric acid (350 mg) in methanol. The solvent was evaporated under reduced pressure and the residue was recrystallized from a mixed solvent of ethanol and water to give the title compound as colorless crystals (yield 793 mg, 29%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:9)

Sources & evidence

ORD record
ord-e629051cd2b6431580f1f86ad5c36b36
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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