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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
ノート
印刷プレビュー

反応式

HRID 2098966 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-87a18c18aeab42adaa71d95634b76307
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08450522B2

反応ノート

読み込み中…

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