Acetic Acid → 5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one acetate

HRID 423223Notes

Reaction equation

HRID 423223 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:21][NH:22]CC2C=CC=CC=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.[C:38]([OH:41])(=[O:40])[CH3:39]>CO>[C:38]([OH:41])(=[O:40])[CH3:39].[NH2:22][CH2:21][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)[O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 666727545-[(R)-2-benzylamino 1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one

Product 1

HCID 666722995-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-hydroxy-1H-quinolin-2-one acetateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-Benzyloxy-5-[(R)-2-(N-benzylamino)-1-(tert-butyldimethylsilanyloxy)ethyl]-1H-quinolin-2-one (100 g, 194 mmol) and acetic acid (17.5 mL, 291 mmol) were dissolved in methanol (1 L). The clear solution was purged with nitrogen and then palladium hydroxide on carbon (20 g, 20 wt. % Pd (dry basis), wet (about 50% water)) was added. Hydrogen gas was bubbled through the stirred solution at room temperature for 6 hours during which time a thick slurry developed. The reaction mixture was then purged with nitrogen and methanol (1 L) was added. The resulting mixture was stirred for about 30 minutes (to dissolve the product) and then the mixture was filtered through a pad of Celite. The filterate was concentrated under reduced pressure to a volume of about 500 mL and, to the resulting slurry, was added ethanol (500 mL). The resulting mixture was again concentrated under reduced pressure to a volume of about 500 mL and the resulting precipitate was collected by filtration and dried to provide the title compound as a yellow-white solid (65 g, 85% yield, >98% purity).

Workup

  1. customThe clear solution was purged with nitrogen
  2. additionpalladium hydroxide on carbon (20 g, 20 wt. % Pd (dry basis), wet (about 50% water)) was added
  3. customHydrogen gas was bubbled through the stirred solution at room temperature for 6 hours during which time a thick slurry
  4. customThe reaction mixture was then purged with nitrogen and methanol (1 L)
  5. additionwas added
  6. dissolutionto dissolve the product) and then the mixture
  7. filtrationwas filtered through a pad of Celite
  8. concentrationThe filterate was concentrated under reduced pressure to a volume of about 500 mL and, to the resulting slurry
  9. additionwas added ethanol (500 mL)
  10. concentrationThe resulting mixture was again concentrated under reduced pressure to a volume of about 500 mL
  11. filtrationthe resulting precipitate was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-b9b1b6c7f0b344bf84a5cb3631bdbddb
Source dataset
uspto-grants-2012_01
Patent number
US08101766B2

Reaction notes

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