Hydrochloric Acid → (S)-2-(6-((2',6'-dimethyl-4'-((1-(methylsulfonyl)piperidin-4-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280643노트

반응식

HRID 2280643 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[C:4]([CH3:19])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][C:28]2[CH:41]=[CH:40][C:31]3[C@H:32]([CH2:35][C:36]([O:38]C)=[O:37])[CH2:33][O:34][C:30]=3[CH:29]=2)[CH:21]=1.[OH-].[Na+].Cl>C(O)C>[CH3:19][C:4]1[CH:5]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([S:15]([CH3:18])(=[O:17])=[O:16])[CH2:11][CH2:10]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][O:27][C:28]2[CH:41]=[CH:40][C:31]3[C@H:32]([CH2:35][C:36]([OH:38])=[O:37])[CH2:33][O:34][C:30]=3[CH:29]=2)[CH:21]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89701796(S)-methyl 2-(6-((2',6'-dimethyl-4'-((1-(methylsulfonyl)piperidin-4-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

생성물 1

HCID 71656907(S)-2-(6-((2',6'-dimethyl-4'-((1-(methylsulfonyl)piperidin-4-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid수율 44%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The crude (S)-methyl 2-(6-((2′,6′-dimethyl-4′-((1-(methylsulfonyl)piperidin-4-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 5a (28 mg, 0.05 mmol) was dissolved in 5 mL of ethanol, followed by addition of 1M aqueous sodium hydroxide solution (0.5 mL, 0.50 mmol). The reaction solution was reacted for 1 hour. 1M hydrochloric acid was added dropwise to the resulting solution to adjust the pH to 5, followed by extraction 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 and the residue was purified using a method of preparative separation to obtain the title compound (S)-2-(6-((2′,6′-dimethyl-4′-((1-(methylsulfonyl)piperidin-4-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 5 (12 mg, yield 44.0%) as a white solid.

후처리

  1. customThe reaction solution was reacted for 1 hour
  2. extractionfollowed by extraction with ethyl acetate (20 mL×2)
  3. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  4. dry with materialdried with anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified
  8. customa method of preparative separation

출처 및 근거

ORD 기록
ord-94aab665bfcc4d5ba800fb491ab0114b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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