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Lithium Hydroxide → (S)-2-(6-((4'-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280665
ノート
印刷プレビュー

反応式

HRID 2280665 の反応式
[CH:1]1([C:4]([N:6]2[CH2:9][CH:8]([O:10][C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]5[CH:39]=[CH:38][C:29]6[C@H:30]([CH2:33][C:34]([O:36]C)=[O:35])[CH2:31][O:32][C:28]=6[CH:27]=5)[CH:19]=4)=[C:13]([CH3:40])[CH:12]=3)[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Li+]>CO>[CH:1]1([C:4]([N:6]2[CH2:9][CH:8]([O:10][C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]5[CH:39]=[CH:38][C:29]6[C@H:30]([CH2:33][C:34]([OH:36])=[O:35])[CH2:31][O:32][C:28]=6[CH:27]=5)[CH:19]=4)=[C:13]([CH3:40])[CH:12]=3)[CH2:7]2)=[O:5])[CH2:3][CH2:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 117699344(S)-methyl 2-(6-((4'-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

生成物 1

HCID 71657093(S)-2-(6-((4'-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid収率 44%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The crude (S)-methyl 2-(6-((4′-((1-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 15b (46 mg, 0.09 mmol) was dissolved in 3 mL of methanol, followed by addition of 1M aqueous lithium hydroxide solution (0.5 mL, 0.50 mmol). The reaction solution was stirred for 3 hours. The resulting solution was concentrated under reduced pressure, 1M hydrochloric acid was added dropwise to adjust the pH to 3, 3 mL of water were added, and then the solution was 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-(cyclopropanecarbonyl)azetidin-3-yl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 15 (20 mg, yield 44.0%) as a yellow solid.

後処理

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

出典と根拠

ORDレコード
ord-f17bf3614d1a4dd893b3ef64a2b1382b
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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