p-Toluenesulfonic acid → HCID 11119733, compound

HRID 850594Notes

Reaction equation

HRID 850594 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][CH2:8][CH2:9][C:10]1([CH3:15])OCC[O:11]1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[CH3:15])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 54181390HCID 54181390, compound

Product 1

HCID 11119733HCID 11119733, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-5 (35 g, 0.1 mol) in 600 mL acetone was added p-toluenesulfonic acid (1 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 2-6 as a yellow oil. TLC Rf =0.31 (silica, 30% ethyl acetate/hexane). 1H NMR (300 MHz, CDCl3, mixture of rotamers) δ 4.20 (m, 2H), 3.92 (s, 0.85H), 3.83 (s, 1.15 H), 3.3 (m, 2H), 2.52 (m, 2H), 2.14 (s, 3H), 1.78 (m, 2H), 1.51-1.42 (3s, 9H), 1.28 (m, 3H).

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-3a4345cec7dd4e0fb32097cce7311abd
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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