(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 2412258Notes

Reaction equation

HRID 2412258 reaction equation
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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-50623f1885e74a14b0d7aa6d325d3b71
Source dataset
uspto-grants-2014_08
Patent number
US08816088B2

Reaction notes

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