Acetic Acid → 5{(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-hydroxyphenylformamide acetate

HRID 2118359Notes

Reaction equation

HRID 2118359 reaction equation
C([N:8]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([S:46]([CH:49]2[CH2:53][CH2:52][CH2:51][CH2:50]2)(=[O:48])=[O:47])[CH:41]=1)[CH2:9][C@@H:10]([C:12]1[CH:13]=[CH:14][C:15]([O:21]CC2C=CC=CC=2)=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=1)[OH:11])C1C=CC=CC=1.[C:54]([OH:57])(=[O:56])[CH3:55]>CCO.[Pd].[OH-].[OH-].[Pd+2]>[C:54]([OH:57])(=[O:56])[CH3:55].[CH:49]1([S:46]([C:42]2[CH:41]=[C:40]([CH2:39][CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][NH:8][CH2:9][C@@H:10]([C:12]3[CH:13]=[CH:14][C:15]([OH:21])=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=3)[OH:11])[CH:45]=[CH:44][CH:43]=2)(=[O:48])=[O:47])[CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 866076805-{(1R)-2-[Benzyl(6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(benzyloxy)phenylformamide

Product 1

HCID 866076815{(1R)-2-[(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-hydroxyphenylformamide acetate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

5-{(1R)-2-[Benzyl(6-{4-[3-(cyclopentylsulfonyl)phenyl]butoxy}hexyl)amino]-1-hydroxyethyl}-2-(benzyloxy)phenylformamide (17 mg) was dissolved in EtOH (10 ml) and glacial acetic acid (1 ml) added. The solution was hydrogenated using 10% palladium on carbon (50% water by weight, 7 mg) and 20% palladium hydroxide on carbon (7 mg) for 20 h. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was purified on an isolute aminopropyl cartridge (2 g), eluting with MeOH-DCM mixtures. Evaporation of the appropriate fractions with AcOH gave the title compound, (5 mg) LCMS RT=2.53 min, ES+ve 561 (MH)+

Workup

  1. customfor 20 h
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified on an isolute aminopropyl cartridge (2 g)
  5. washeluting with MeOH-DCM mixtures
  6. customEvaporation of the appropriate fractions with AcOH

Sources & evidence

ORD record
ord-b06b66cad84944fe97bb40d75f2209cd
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

Loading…