Ethanol → 8-Hydroxy-5-((1R)-1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)quinolin-2(1H)-one acetate

HRID 749230Notes

Reaction equation

HRID 749230 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:47])[CH2:21][N:22](CC2C=CC=CC=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.C([OH:50])C>C(O)(=O)C.[Pd]>[C:30]([OH:50])(=[O:29])[CH3:31].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:47])[CH2:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2

Participants

5

Reactant 2

HCID 702EthanolHCID 115564068-(Benzyloxy)-5-((1R)-2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)quinolin-2(1H)-one

Product 1

HCID 693188928-Hydroxy-5-((1R)-1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)quinolin-2(1H)-one acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 8-(benzyloxy)-5-((1R)-2-{benzyl[6-(4-phenylbutoxy)hexyl]amino}-1-hydroxyethyl)quinolin-2(1H)-one (33 mg) in ethanol (15 ml) and acetic acid (0.4 ml) was stirred under hydrogen in the presence of palladium on charcoal (10 mg) for 4 h. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by chromatography (SPE, gradient from DCM to DCM-MeOH—NH3(aq) 100:10:1) to give the title compound (19.5 mg).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography (SPE, gradient from DCM to DCM-MeOH—NH3(aq) 100:10:1)

Sources & evidence

ORD record
ord-1fecca457b294012b33776fc4210e36b
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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