Trifluoroacetic acid → HCID 66925136, compound

HRID 554400Notes

Reaction equation

HRID 554400 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:22][N:23](C)[C:24](=O)OC(C)(C)C)=[CH:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:14][C:13]([CH2:22][NH:23][CH3:24])=[CH:12]2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86620742HCID 86620742, compound

Product 1

HCID 66925136HCID 66925136, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {{1-[(3-chlorophenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl}methylcarbamate (726 mg) was dissolved in dichloromethane (3 ml), trifluoroacetic acid (2 ml) was added at 0° C., and the mixture was stirred at room temperature for 15 min. The reaction solution was basified by the dropwise addition to 6% aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate-methanol (19:1). The obtained pale-yellow oil was dissolved in ethyl acetate, 4 mol/L hydrogen chloride-ethyl acetate solution was added, activated carbon was added and the mixture was filtered through celite. The celite was washed sufficiently with methanol and the filtrate was concentrated under reduced pressure. The residue was crystallized from ethyl acetate and hexane, and recrystallized from ethyl acetate-ethanol to give the title compound as colorless crystals (yield 324 mg, 52%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with ethyl acetate-methanol (19:1)
  6. dissolutionThe obtained pale-yellow oil was dissolved in ethyl acetate
  7. addition4 mol/L hydrogen chloride-ethyl acetate solution was added
  8. additionwas added
  9. filtrationthe mixture was filtered through celite
  10. washThe celite was washed sufficiently with methanol
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe residue was crystallized from ethyl acetate and hexane
  13. customrecrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-60e73f3071904886ade0f8d681369f9d
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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