N-{5-((1R)-1-Hydroxy-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethyl)-2-[(phenylmethyl)oxy]phenyl}-N-(phenylmethyl)methanesulfonamide → (R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

HRID 2118348Notes

Reaction equation

HRID 2118348 reaction equation
[OH:1][C@H:2]([C:14]1[CH:15]=[CH:16][C:17]([O:32]CC2C=CC=CC=2)=[C:18]([N:20](CC2C=CC=CC=2)[S:21]([CH3:24])(=[O:23])=[O:22])[CH:19]=1)[CH2:3][NH:4][C@@H](C1C=CC=CC=1)CO>[Pd].CCO.CC(O)=O.[OH-].[Pd+2].[OH-]>[NH2:4][CH2:3][C@@H:2]([C:14]1[CH:15]=[CH:16][C:17]([OH:32])=[C:18]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:19]=1)[OH:1]

Participants

6

Reactant 1

HCID 69120074N-{5-((1R)-1-Hydroxy-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethyl)-2-[(phenylmethyl)oxy]phenyl}-N-(phenylmethyl)methanesulfonamide

Product 1

HCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To an evacuated flask containing palladium hydroxide (70.8 mg) and palladium on carbon [50% water by weight] (70.8 mg) was added a solution of N-{5-((1R)-1-hydroxy-2-{[(1S)-2-hydroxy-1-phenylethyl]amino}ethyl)-2-[(phenylmethyl)oxy]phenyl}-N-(phenylmethyl)methanesulfonamide (354 mg) in EtOH (15 ml) and AcOH (3 ml). The mixture was hydrogenated for 19 h. The catalysts were filtered off and the filtrate concentrated in vacuo. The mixture was purified by column chromatography (Oasis cartridge, 0 to 50% MeOH in water) to afford the title compound. LCMS RT=0.35 min

Workup

  1. filtrationThe catalysts were filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe mixture was purified by column chromatography (Oasis cartridge, 0 to 50% MeOH in water)

Sources & evidence

ORD record
ord-21e21cfd0f30468889612898564549a2
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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