(3-{(S)-2-([R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic acid → (3-{(S)-2-[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]propyl}phenyl)acetic acid

HRID 1468501ノート

反応式

HRID 1468501 の反応式
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:21][NH:22][C@@H:23]([CH3:35])[CH2:24][C:25]2[CH:26]=[C:27]([CH2:31][C:32]([OH:34])=[O:33])[CH:28]=[CH:29][CH:30]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1>CCO.[Pd]>[Si:37]([O:36][C@H:20]([C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:19])[NH:17]2)[CH2:21][NH:22][C@@H:23]([CH3:35])[CH2:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([OH:34])=[O:33])[CH:28]=[CH:29][CH:30]=1)([C:40]([CH3:43])([CH3:41])[CH3:42])([CH3:39])[CH3:38]

参加物

4

反応物 1

HCID 66770367(3-{(S)-2-([R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic acid

生成物 1

HCID 66770193(3-{(S)-2-[(R)-2-(tert-butyldimethylsilanyloxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino]propyl}phenyl)acetic acid収率 45.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A solution of (3-{(S)-2-[(R)-2-(8-benzyloxy-2-oxo-1,2-dihydroquinolin-5-yl)-2-(tert-butyldimethylsilanyloxy)ethylamino]propyl}phenyl)acetic acid (˜1.3 mmol) in EtOH (8 mL) was purged with dry nitrogen and then palladium on carbon (10%, ˜50% water, Degussa type, 300 mg) was added. This mixture was purged with hydrogen and then stirred under an atmosphere of hydrogen (balloon) for 1 h. The mixture was then filtered through Celite and the filter bed washed with MeOH (20 mL) and EtOAc (20 mL). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography (0-20% MeOH in DCM) to give the title compound (300 mg, 40% yield) as a yellow solid.

後処理

  1. customThis mixture was purged with hydrogen
  2. filtrationThe mixture was then filtered through Celite
  3. washthe filter bed washed with MeOH (20 mL) and EtOAc (20 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel flash chromatography (0-20% MeOH in DCM)

出典と根拠

ORDレコード
ord-40bb170ed9cb48ec91995139108d0f09
出典データセット
uspto-grants-2015_04
特許番号
US09000173B2

反応ノート

読み込み中…