Sodium Hydroxide → [2-(7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid

HRID 1188993ノート

反応式

HRID 1188993 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:25]=[N:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([O:20]CC)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.[OH-].[Na+]>O1CCCC1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:23][C:24]2[CH:25]=[N:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[CH2:15][N:16]=1)=[CH:8]2

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 70963862Ethyl [2-(7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate

生成物 1

HCID 67118501[2-(7-Methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetic acid収率 93%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl [2-(7-methoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (11.06 g) was dissolved in a mixture of tetrahydrofuran (100 mL) and ethanol (100 mL). To the mixture was added 1M aqueous sodium hydroxide solution (37 mL) and the mixture was stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure. The residue was dissolved in water and 1M hydrochloric acid (37 mL) was added to the mixture. The resulting yellow suspension was filtered to collect a yellow solid. The solid was dissolved in ethyl acetate-tetrahydrofuran. The solution was dried over magnesium sulfate, filtered and concentrated. The residual solid was washed with diethyl ether to give the title compound (9.65 g, 93%) as a yellow solid. MS 462 (MH+).

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. addition1M hydrochloric acid (37 mL) was added to the mixture
  4. filtrationThe resulting yellow suspension was filtered
  5. customto collect a yellow solid
  6. dissolutionThe solid was dissolved in ethyl acetate-tetrahydrofuran
  7. dry with materialThe solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washThe residual solid was washed with diethyl ether

出典と根拠

ORDレコード
ord-c52ec2425e764205b9416313106d561f
出典データセット
uspto-grants-2014_03
特許番号
US08673942B2

反応ノート

読み込み中…