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

반응식

HRID 229860 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-4a5cf6c4afb64be6b49837ecfc880f33
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563910B2

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