Hydrogen chloride-ethyl acetate → HCID 67397811, compound

HRID 1426787Notes

Reaction equation

HRID 1426787 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([N:12]1[C:16]([C:17]2[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][C:14]([CH2:24][N:25](C)[C:26](=O)OC(C)(C)C)=[CH:13]1)(=[O:11])=[O:10].C(OCC)(=O)C.[ClH:40]>C(OCC)(=O)C.CO>[ClH:40].[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([N:12]1[C:16]([C:17]2[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][C:14]([CH2:24][NH:25][CH3:26])=[CH:13]1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67396338HCID 67396338, compound

Product 1

HCID 67397811HCID 67397811, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl ({1-[(2,5-difluorophenyl)sulfonyl]-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl}methyl)methylcarbamate (160 mg) was dissolved in ethyl acetate (5 mL) and methanol (3 mL), and 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) was 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. The free base was dissolved in ethyl acetate. 4 mol/L Hydrogen chloride-ethyl acetate solution was added and the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from ethanol to give the title compound as colorless crystals (yield 45.9 mg, 33%).

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-7a8b975408dc4cdfa0bf43ff1ea8d755
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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