Ethanol → HCID 69318858, compound

HRID 749235Notes

Reaction equation

HRID 749235 reaction equation
C([N:8]([CH2:30][C@@H:31]([C:33]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]2C=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][O:15][CH2:16][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([OH:54])C>C(O)(=O)C.[Pd]>[C:44]([OH:54])(=[O:43])[CH3:45].[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][O:15][CH2:16][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

5

Reactant 2

HCID 702EthanolHCID 69318909HCID 69318909, compound

Product 1

HCID 69318858HCID 69318858, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-{[6-(Benzyl{(2R)-2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino)hexyl]oxy}butyl)benzenesulfonamide (10 mg) in ethanol (10 ml) and acetic acid (0.1 ml) was stirrer under hydrogen in the presence of palladium on charcoal (5 mg) for 2 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) and freeze-dried from water-acetic acid to give the title compound (5.8 mg).

Workup

  1. customfor 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (SPE, gradient from DCM to DCM-MeOH—NH3(aq) 100:10:1)
  5. dry with materialfreeze-dried from water-acetic acid

Sources & evidence

ORD record
ord-e110201292874f12902cb0960620f9fd
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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