Sodium Hydroxide → 2-((S)-6-((2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid

HRID 2280632ノート

反応式

HRID 2280632 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][C@@H:9]2[CH2:13][CH2:12][O:11][CH2:10]2)[CH:5]=[C:4]([CH3:14])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[C@H:27]([CH2:30][C:31]([O:33]C)=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1.[OH-].[Na+]>CO>[CH3:14][C:4]1[CH:5]=[C:6]([O:8][C@@H:9]2[CH2:13][CH2:12][O:11][CH2:10]2)[CH:7]=[C:2]([CH3:1])[C:3]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:22][C:23]2[CH:36]=[CH:35][C:26]3[C@H:27]([CH2:30][C:31]([OH:33])=[O:32])[CH2:28][O:29][C:25]=3[CH:24]=2)[CH:16]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 117699407methyl 2-((S)-6-((2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

生成物 1

HCID 716568152-((S)-6-((2',6'-dimethyl-4'-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid収率 77.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl 2-((S)-6-((2′,6′-dimethyl-4′-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 2d (201 mg, 0.41 mmol) was dissolved in 15 mL of methanol. The reaction solution was added with 2M aqueous sodium hydroxide solution (2 mL, 4.10 mmol) and stirred for 3 hours. The resulting solution was concentrated under reduced pressure, mixed with 10 mL of water, and 1M hydrochloric acid was added dropwise to adjust the pH to 2-3. 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 2-((S)-6-((2′,6′-dimethyl-4′-(((R)-tetrahydrofuran-3-yl)oxy)biphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetic acid 2 (150 mg, yield 77.1%) as a white solid.

後処理

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. additionmixed with 10 mL of water, and 1M hydrochloric acid
  3. additionwas added dropwise
  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-dd393e242934409c9f4d03c6ad3cefb3
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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