(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 1468501노트

반응식

HRID 1468501 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-40bb170ed9cb48ec91995139108d0f09
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000173B2

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