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Lithium Hydroxide → 2-((S)-6-((2',6'-dimethyl-4'-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280647
ノート
印刷プレビュー

反応式

HRID 2280647 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]2)[CH:5]=[C:4]([CH3:18])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]2[CH:40]=[CH:39][C:30]3[C@H:31]([CH2:34][C:35]([O:37]C)=[O:36])[CH2:32][O:33][C:29]=3[CH:28]=2)[CH:20]=1.[OH-].[Li+]>O1CCCC1.CO>[CH3:18][C:4]1[CH:5]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][O:26][C:27]2[CH:40]=[CH:39][C:30]3[C@H:31]([CH2:34][C:35]([OH:37])=[O:36])[CH2:32][O:33][C:29]=3[CH:28]=2)[CH:20]=1
参加物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 89701802methyl 2-((S)-6-((2',6'-dimethyl-4'-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

生成物 1

HCID 716569102-((S)-6-((2',6'-dimethyl-4'-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid収率 101.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

Methyl 2-((S)-6-((2′,6′-dimethyl-4′-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 8b (30 mg, 0.05 mmol) was dissolved in 2 mL of a mixture of the solvents tetrahydrofuran and methanol (V/V=1:1), followed by addition of 1M aqueous lithium hydroxide solution (0.1 mL, 0.10 mmol). The reaction solution was stirred for 2 hours. The resulting solution was concentrated under reduced pressure, 1M hydrochloric acid was added dropwise to adjust the pH to 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 2-((S)-6-((2′,6′-dimethyl-4′-(((S)-1-(methylsulfonyl)pyrrolidin-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 8 (28 mg, yield 94.2%) as a white solid.

後処理

  1. concentrationThe resulting solution was concentrated under reduced pressure, 1M hydrochloric acid
  2. additionwas added dropwise
  3. extractionextracted with ethyl acetate (20 mL×2)
  4. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  5. dry with materialdried with anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-5d1e83ac022041b7ae66e80b5aae23d8
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139548B2

反応ノート

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