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

Reaktionsgleichung

Reaktionsgleichung von HRID 229860
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4a5cf6c4afb64be6b49837ecfc880f33
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07563910B2

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