Hydrogen chloride-ethyl acetate → HCID 66925030, compound

HRID 554450Notes

Reaction equation

HRID 554450 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([CH3:24])([OH:23])[CH3:22])[CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:25][NH:26][C:27](=O)OC(C)(C)C)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=O)C.Cl>C(O)C>[CH3:27][NH:26][CH2:25][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:11]([S:12]([C:15]2[CH:16]=[C:17]([C:21]([OH:23])([CH3:24])[CH3:22])[CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:10]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86620791HCID 86620791, compound

Product 1

HCID 66925030HCID 66925030, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl [1-(5-phenyl-1-{[3-(1-methyl-1-hydroxyethyl)phenyl]sulfonyl}-1H-pyrrol-3-yl)methyl]carbamate (334 mg) in ethanol (4 mL) was added 4 mol/L hydrogen chloride-ethyl acetate solution (4.0 mL) and the mixture was stirred at room temperature for 3 hr. After the reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate) to give the title compound as a white solid (yield 203 mg, 76%).

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate solution
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-071724f9d42748b0a0c2b84d5f29d4ed
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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