p-Toluenesulfonic acid → HCID 59899168, compound

HRID 2227266Notes

Reaction equation

HRID 2227266 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH:5]([C:23]1[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)[CH2:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][C:16]2([CH3:21])OCC[O:17]2)[C:10]1=[O:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH:5]([C:23]1[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)[CH2:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][CH2:15][C:16](=[O:17])[CH3:21])[C:10]1=[O:22]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59899169HCID 59899169, compound

Product 1

HCID 59899168HCID 59899168, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-12 (440 mg) in acetone (30 mL) was added p-toluenesulfonic acid (270 mg) and the mixture was heated at reflux for 2 h, then cooled to ambient temperature for 3 h. The reaction mixture was concentrated at reduced pressure. The residue was diluted with ethyl acetate and 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 1-13 as an oil, which was used in the next step 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-321608d1678c4544a505a9f4544fd605
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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