p-Toluenesulfonic acid → HCID 86758295, compound

HRID 2227273Notes

Reaction equation

HRID 2227273 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:25]1[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]([CH3:15])[CH2:13][C@H:12]([CH2:16][CH2:17][C:18]2([CH3:23])OCC[O:19]2)[C:11]1=[O:24])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:3][C:4](=[O:33])[CH:5]([C:25]1[CH:26]=[N:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]([CH3:15])[CH2:13][CH:12]([CH2:16][CH2:17][C:18](=[O:19])[CH3:23])[C:11]1=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86758296HCID 86758296, compound

Product 1

HCID 86758295HCID 86758295, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-4 (1.1 g) in acetone (50 mL) was added p-toluenesulfonic acid (470 mg) and the mixture was heated at reflux for 2 h, then cooled to ambient temperature. The reaction mixture was concentrated at reduced pressure and the residue was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure to give 3-5 as an oil , which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was concentrated at reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe reaction mixture was filtered
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-9707349042a646b3a1ccced9cae61950
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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