Water → 3-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester

HRID 398443노트

반응식

HRID 398443 반응식
[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:11]1[CH:16]=[CH:15][C:14](Cl)=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:22][S:23]([O-:25])=[O:24].[Na+].C(OCC)(=O)C.O>CS(C)=O>[CH3:1][O:2][C:3](=[O:21])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:23]([CH3:22])(=[O:25])=[O:24])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2733271Sodium methanesulfinateHCID 120695062-(4-Chloro-3-nitrophenyl)-3-cyclopentyl-propionic acid methyl ester

생성물 1

HCID 120695073-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester수율 84%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 2-(4-chloro-3-nitrophenyl)-3-cyclopentyl-propionic acid methyl ester (1.00 g, 3.21 mmol) and sodium methanesulfinate (0.36 g, 3.53 mmol) in dimethyl sulfoxide (3 mL) was heated at 130° C. for 5 h. The black reaction mixture was then poured over ice (20 g), resulting in the formation of a brown sticky substance. The resulting mixture was then treated with ethyl acetate (50 mL) and water (50 mL), and the layers were separated. The aqueous layer was further extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester (0.95 g, 84%) as a yellow gel: FAB-HRMS m/e calcd for C16H21NO6S (M+H)+ 356.1169, found 356.1175.

후처리

  1. customThe black reaction mixture
  2. customresulting in the formation of a brown sticky substance
  3. customthe layers were separated
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-90ca5bdae88e437c93415864adb4ddba
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610846B1

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