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Cesium carbonate → methyl ((1R)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetate

HRID 2098966
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HRID 2098966 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@H:8]2[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22]([O:26][C:27]1[CH:32]=[C:31]([CH2:33]Cl)[CH:30]=[CH:29][C:28]=1[C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[F:43])[CH2:23][CH2:24][CH3:25]>CN(C=O)C.O>[CH2:22]([O:26][C:27]1[CH:32]=[C:31]([CH2:33][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C@@H:8]3[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=2)[CH:30]=[CH:29][C:28]=1[C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[F:43])[CH2:23][CH2:24][CH3:25].[CH2:22]([O:26][C:27]1[CH:32]=[C:31]([CH2:33][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C@H:8]3[CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=2)[CH:30]=[CH:29][C:28]=1[C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[F:43])[CH2:23][CH2:24][CH3:25]
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참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 577055582-(Butyloxy)-4-(chloromethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenylHCID 59590768(S)-methyl 2-(6-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate

생성물 2

HCID 59590805methyl ((1R)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetate
HCID 59590932
methyl ((1S)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetate

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To flask containing (R) or (S)-methyl 2-(6-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate (1.5) (0.0100 g, 0.0485 mmol) and cesium carbonate (0.0205 g, 0.0630 mmol) in DMF (1 mL) was added 2-(butyloxy)-4-(chloromethyl)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl (D) (0.0188 g, 0.0582 mmol). The reaction was then stirred overnight, diluted with water, and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, concentrated, and then purified by silica gel chromatography (0 to 20% EtOAc/Hexane) to provide methyl ((1R)-6-(((2-(butyloxy)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetate or methyl ((1S)-6-(((2-(butyloxy)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetate 17.1.

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (0 to 20% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-87a18c18aeab42adaa71d95634b76307
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450522B2

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