{5-{(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl}-2-[(phenylmethyl)oxy]phenyl}formamide → (5-{(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)formamide

HRID 494167Notes

Reaction equation

HRID 494167 reaction equation
[C:1]1([CH2:7][N:8]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:9][C@@H:10]([C:12]2[CH:13]=[CH:14][C:15]([O:21]CC3C=CC=CC=3)=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=2)[OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CCOC(C)=O.CCO.[Pd]>[C:1]1([CH2:7][N:8]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:9][C@@H:10]([C:12]2[CH:13]=[CH:14][C:15]([OH:21])=[C:16]([NH:18][CH:19]=[O:20])[CH:17]=2)[OH:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 86606166{5-{(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl}-2-[(phenylmethyl)oxy]phenyl}formamideHCID 178418361HCID 178418361, compound

Product 1

HCID 86606167(5-{(1R)-2-[Bis(phenylmethyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)formamideYield 33.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of {5-{(1R)-2-[bis(phenylmethyl)amino]-1-hydroxyethyl}-2-[(phenylmethyl)oxy]phenyl}formamide (1.40 g) in EtOAc (15 ml) and EtOH (15 ml) was hydrogenated over 10% palladium on carbon (140 mg). When hydrogen uptake had ceased the mixture was filtered through celite, the solvent evaporated in vacuo and the residue purified on a silica SPE bond elut cartridge (70 g) using a gradient of 0% to 5% MeOH in DCM (Gradmaster™). The appropriate fractions were evaporated in vacuo to give the title compound (380 mg). LCMS RT=2.17 min.

Workup

  1. filtrationwas filtered through celite
  2. customthe solvent evaporated in vacuo
  3. customthe residue purified on a silica SPE bond elut cartridge (70 g)
  4. customThe appropriate fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-bad7811d5a474366998c6e16dfd7e383
Source dataset
uspto-grants-2009_05
Patent number
US07538127B2

Reaction notes

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