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 2280639노트

반응식

HRID 2280639 반응식
[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]

참가 물질

4

반응물 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

생성물 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 acid수율 51%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-980fbb82f567498f81e0dab86059f364
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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