p-Toluenesulfonic acid → HCID 68838780, compound

HRID 2105768Notes

Reaction equation

HRID 2105768 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([CH2:8][C:9]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[O:19][CH3:20])=O)[C:5](=O)[CH3:6].[CH:22]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:2][C:3]([C:4]1[CH:8]=[C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[O:19][CH3:20])[N:29]([CH2:28][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:5]=1[CH3:6])=[O:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 76688CyclohexanemethylamineHCID 68842837HCID 68842837, compound

Product 1

HCID 68838780HCID 68838780, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2 g of -[2-(2,5-Dimethoxy-phenyl)-2-oxo-ethyl]-3-oxo-butyric acid methyl ester in methanol was added 0.88 ml of cyclohexanemethylamine and 40 mg of p-toluene sulfonic acid. The reaction mixture was then heated at reflux for 2 days. After such time the reaction mixture was allowed to cool to room temperature before being concentrated in vacuo and purified by column chromatography to give 2.3 g of the title compound; MS (ISP) 372.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 2 days
  3. concentrationbefore being concentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-df920ef10d844aca98ee452a9a575a72
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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