Hexane → 2-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

HRID 2245510노트

반응식

HRID 2245510 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][C:21](=[O:38])[CH:22](OS(C(F)(F)F)(=O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCCCCC>CC(C)=O.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:38])[CH:22]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

7

반응물 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 225235-NitroindoleHCID 13388932alpha-(Trifluoromethylsulfonyloxy)hydrocinnamic acid methyl ester

생성물 1

HCID 592167062-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

To 5-nitro-1H-indole (5.18 g, 31.93 mmol) in acetone (200 ml) at ambient temperature under a nitrogen atmosphere was added cesium carbonate (21.80 g, 67.06 mmol) followed by 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (10.96 g, 35.13 mmol). The resulting dark red mixture was stirred for 5 hours, concentrated in vacuo to a brown powder which was then partitioned between H2O (100 ml) and EtOAc (300 ml). All organics were combined, extracted with brine (250 ml), dried with MgSO4, filtered, and concentrated in vacuo. Gradient SiO2 chromatography (Hexane:EtOAc) afforded 2-(5-nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester as an opaque syrup (5.91 g, 57% yield): MS (ESI) m/z 325, MS (ESI) m/z 323.

후처리

  1. concentrationconcentrated in vacuo to a brown powder which
  2. customwas then partitioned between H2O (100 ml) and EtOAc (300 ml)
  3. extractionextracted with brine (250 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e44e252b26d04892bc29f7c29ccd6f71
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683091B2

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