Water → HCID 19066032, compound

HRID 2377234Notes

Reaction equation

HRID 2377234 reaction equation
[C:1]12([O:14]CCO1)[C:9]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:10])[C:4]=1[CH2:3][CH2:2]2.[C:15](Cl)(=[O:17])[CH3:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>N1C=CC=CC=1>[O:14]=[C:1]1[C:9]2[C:4](=[C:5]([NH:10][C:15](=[O:17])[CH3:16])[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6367Acetyl chlorideHCID 69201851HCID 69201851, compound

Product 1

HCID 19066032HCID 19066032, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a vigorously stirred solution of Example 25 (3.9 g, 20.6 mmol) in pyridine (40 mL) was slowly added acetyl chloride (1.6 mL, 22.6 mmol). The reaction was stirred at room temperature for about 15 minutes and then the solvent was removed under vacuum. The residue was dissolved in acetone (38 mL) and water (12 mL) and p-toluenesulfonic acid (3.9 g, 20.6 mmol) was added. The mixture was heated to reflux for about 1 hour, cooled, and concentrated under vacuum. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (1:1) as the mobile phase to provide the desired product. MS (ESI): m/z 188 (M−H)−.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in acetone (38 mL)
  3. temperatureThe mixture was heated
  4. temperatureto reflux for about 1 hour
  5. temperaturecooled
  6. concentrationconcentrated under vacuum
  7. extractionThe aqueous layer was extracted with ethyl acetate
  8. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-954d6ec4568243a4b76a63b44ffd202d
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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