p-Toluenesulfonic acid → 2-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester

HRID 229860

Reaction equation

HRID 229860 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][C:17]([F:20])([F:19])[F:18])[C:5](=O)[CH3:6].[CH2:23]([NH2:29])[C@H:24]1[O:28][CH2:27][CH2:26][CH2:25]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:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][C:17]([F:20])([F:19])[F:18])[N:29]([CH2:23][C@@H:24]2[CH2:25][CH2:26][CH2:27][O:28]2)[C:5]=1[CH3:6])=[O:22]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 641530(S)-(+)-TetrahydrofurfurylamineHCID 690212293-Oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl ester

Product 1

HCID 690232432-methyl-1-[(S)-1-(tetrahydro-furan-2-yl)methyl]-5-(2-trifluoromethoxy-phenyl)-1H-pyrrole-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 250 mg of 3-oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl ester in methanol was added 84 μl of (S)-tetrahydrofurfurylamine and 5 mg of p-toluene sulfonic acid. The reaction mixture was then heated at reflux for 24 hours. 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 171 mg of the title compound; MS (EI) 383.1 (M)+.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureat reflux for 24 hours
  3. concentrationbefore being concentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-4a5cf6c4afb64be6b49837ecfc880f33
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Linked notes

Loading…