p-Toluenesulfonic acid → HCID 86756578, compound

HRID 322081Notes

Reaction equation

HRID 322081 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH:5]([N:7]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][CH2:9][CH2:10][C:11]1([CH3:16])OCC[O:12]1)[CH3:6])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([N:7]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:8][CH2:9][CH2:10][C:11](=[O:12])[CH3:16])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70244313HCID 70244313, compound

Product 1

HCID 86756578HCID 86756578, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-5 (13.9 g, 0.040 mol) in 100 mL acetone was added p-toluenesulfonic acid (0.05 g). The mixture was heated at reflux for 2 h. After cooling, the mixture was evaporated to one-fifth its initial volume, diluted with EtOAc and then washed with sat. NaHCO3, brine, and dried over Na2SO4. Evaporative removal of the solvent gave 4-6 as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. customthe mixture was evaporated to one-fifth its initial volume
  5. additiondiluted with EtOAc
  6. washwashed with sat. NaHCO3, brine
  7. dry with materialdried over Na2SO4
  8. customEvaporative removal of the solvent

Sources & evidence

ORD record
ord-2789482bcbbe4083aa7bc44809d4ce4d
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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