Acetic Acid → 3-{3-[(7-{[(2R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}heptyl)oxy]propyl}benzenesulfonamide acetate

HRID 749258Notes

Reaction equation

HRID 749258 reaction equation
C([N:8]([CH2:30][C@@H:31]([C:33]1[CH:42]=[CH:41][C:40]([O:43]CC2C=CC=CC=2)=[C:39]2[C:34]=1[CH:35]=[CH:36][C:37](=[O:51])[NH:38]2)[OH:32])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)C1C=CC=CC=1.[C:52]([O:55]CC)(=[O:54])[CH3:53].C(O)(=O)C>C(O)C.[Pd].[OH-].[OH-].[Pd+2]>[C:52]([OH:55])(=[O:54])[CH3:53].[OH:32][C@H:31]([C:33]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]2[C:34]=1[CH:35]=[CH:36][C:37](=[O:51])[NH:38]2)[CH2:30][NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 693162143-(3-{[7-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide

Product 1

HCID 693222853-{3-[(7-{[(2R)-2-Hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}heptyl)oxy]propyl}benzenesulfonamide acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(3-{[7-(benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)heptyl]oxy}propyl)benzenesulfonamide (36 mg) in ethanol (10 ml) with ethyl acetate (2 ml) and glacial acetic acid (1 ml) was hydrogenated using 10% palladium on carbon (50% water by weight, 10 mg) and 20% palladium hydroxide on carbon (10 mg) for 19 h. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified on an aminopropyl SPE cartridge (2 g), eluting with methanol-dichloromethane mixtures. Evaporation of the appropriate fractions with glacial acetic acid gave the title compound (15 mg). LCMS RT=2.26 min ES+ve m/z 532 (MH)+

Workup

  1. customfor 19 h
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified on an aminopropyl SPE cartridge (2 g)
  5. washeluting with methanol-dichloromethane mixtures
  6. customEvaporation of the appropriate fractions with glacial acetic acid

Sources & evidence

ORD record
ord-f8b9915ba1a046f2ace7df6af5b37163
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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