p-Toluenesulfonic acid → 5-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-dihydro-furan-2-one

HRID 11715노트

반응식

HRID 11715 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[C:6]([CH:8]([OH:14])[CH2:9][CH2:10][C:11](O)=[O:12])[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH2:16][C:17]([N:19]2[CH2:24][C@H:23]([CH3:25])[N:22]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:21][C@H:20]2[CH3:34])=[O:18])=[C:6]([CH:8]2[O:14][C:11](=[O:12])[CH2:10][CH2:9]2)[CH:7]=1

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 696554904-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-hydroxy-butyric Acid

생성물 1

HCID 696557095-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-dihydro-furan-2-one수율 109.5%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of 4-(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-4-hydroxy-butyric acid (0.050 g, 0.10 mmol) in toluene (5 mL) was added p-toluene sulfonic acid (0.040 g) and the reaction was stirred at reflux for 4 hours. The reaction was cooled, diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Trituration in diethyl ether/hexanes gave the title compound (0.052 g, LRMS: 475.2, 477.3).

후처리

  1. temperatureat reflux for 4 hours
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f091ce2afc854a4c8b9d7b72de16fbe9
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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