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Lithium Hydroxide → ((1S)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetic acid

HRID 2098967
ノート
印刷プレビュー

反応式

HRID 2098967 の反応式
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][C@H:20]3[CH2:23][C:24]([O:26]C)=[O:25])=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:7]=1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[F:36])[CH2:2][CH2:3][CH3:4].[OH-].[Li+]>C1COCC1.CO>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][C@@H:20]3[CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:7]=1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[F:36])[CH2:2][CH2:3][CH3:4].[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][C@H:20]3[CH2:23][C:24]([OH:26])=[O:25])=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:7]=1[C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:29]=1[F:36])[CH2:2][CH2:3][CH3:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 59590932methyl ((1S)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetate

生成物 2

HCID 44223268((1R)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetic acidHCID 44223269((1S)-6-(((2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetic acid
収率 84.4%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

反応条件

温度
23 °C

実験手順

To a solution of 17.1 (0.024 g, 0.0485 mmol) in THF/MeOH (2/1) (1.5 mL) was added lithium hydroxide (0.50 mL, 0.50 mmol). The resulting mixture was stirred overnight at 23° C., quenched with excess 1N HCl, and extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes) to afford ((1R)-6-(((2-(butyloxy)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetic acid or ((1S)-6-(((2-(butyloxy)-2′-fluoro-5′-(methyloxy)-1,1′-biphenyl-4-yl)methyl)oxy)-2,3-dihydro-1H-inden-1-yl)acetic acid 17 (0.0098 g, 42% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.26-7.31 (1H, m), 7.15 (1H, d, J=7.8 Hz), 7.00-7.09 (3H, m), 6.81-6.90 (4H, m), 5.07 (2H, s), 4.00 (2H, t, J=6.5 Hz), 3.80 (3H, s), 3.59 (1H, m), 2.78-2.94 (3H, m), 2.55-2.40 (2H, m), 1.86-1.76 (1H, m), 1.64-1.71 (2H, m), 1.33-1.43 (2H, m), 0.89 (3H, t, J=7.4 Hz).

後処理

  1. customquenched with excess 1N HCl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0 to 40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-62b6f9598fb746cea25a7429c1daa031
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…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート