Tetrahydrofuran → {2-[5-{[6-(Methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid

HRID 1042151ノート

反応式

HRID 1042151 の反応式
C([O:3][C:4](=[O:37])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][C:21]2[CH:22]=[N:23][C:24]([CH2:27][O:28][CH3:29])=[CH:25][CH:26]=2)=[CH:15][C:14]=3[O:30][CH:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)=[N:8][CH2:7]1)C.[OH-].[Na+].O1CCCC1>C(O)C>[CH3:29][O:28][CH2:27][C:24]1[N:23]=[CH:22][C:21]([O:20][C:16]2[CH:17]=[C:18]3[C:13](=[C:14]([O:30][CH:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:15]=2)[NH:12][C:11]([C:9]2[S:10][CH:6]([CH2:5][C:4]([OH:37])=[O:3])[CH2:7][N:8]=2)=[CH:19]3)=[CH:26][CH:25]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58081032ethyl{2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate

生成物 1

HCID 66726112{2-[5-{[6-(Methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid収率 71.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of ethyl{2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(tetrahydro-2H-pyran-4-yloxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (1.04 g), 1M aqueous sodium hydroxide solution (6 mL), tetrahydrofuran (10 mL), and ethanol (10 mL) was stirred at room temperature for 1 hr. The reaction solution was concentrated under reduced pressure, water was added, and the mixture was washed with ethyl acetate. The aqueous layer was neutralized with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (700 mg, yield 71%) as a white amorphous solid.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure, water
  2. additionwas added
  3. washthe mixture was washed with ethyl acetate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-53577185ad5f48faa8926a0481bfa8cd
出典データセット
uspto-grants-2013_10
特許番号
US08557805B2

反応ノート

読み込み中…