Sodium Hydroxide → (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280639ノート

反応式

HRID 2280639 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][C:30]4[CH:43]=[CH:42][C:33]5[C@H:34]([CH2:37][C:38]([O:40]C)=[O:39])[CH2:35][O:36][C:32]=5[CH:31]=4)[CH:23]=3)=[C:17]([CH3:44])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]([CH3:44])[C:18]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][C:30]4[CH:43]=[CH:42][C:33]5[C@H:34]([CH2:37][C:38]([OH:40])=[O:39])[CH2:35][O:36][C:32]=5[CH:31]=4)[CH:23]=3)=[C:19]([CH3:21])[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 89701758methyl (S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

生成物 1

HCID 71656816(S)-2-(6-((4'-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid収率 51%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl (S)-2-(6-((4′-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3j (26 mg, 0.04 mmol) was dissolved in 5 mL of methanol, followed by addition of 1M aqueous sodium hydroxide solution (0.5 mL, 0.43 mmol). The reaction solution was reacted for 1.5 hours. The solution was concentrated under reduced pressure, mixed with 3 mL of water, 1M citric acid was added dropwise to adjust the pH to 4-5, and extracted with ethyl acetate (20 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (S)-2-(6-((4′-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 3 (12 mg, yield 47.4%) as a white solid.

後処理

  1. customThe reaction solution was reacted for 1.5 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. additionmixed with 3 mL of water, 1M citric acid
  4. additionwas added dropwise
  5. extractionextracted with ethyl acetate (20 mL×2)
  6. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  7. dry with materialdried with anhydrous magnesium sulphate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-980fbb82f567498f81e0dab86059f364
出典データセット
uspto-grants-2015_09
特許番号
US09139548B2

反応ノート

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