{2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-nitro-phenyl)-ethylcarbamoyl]-ethyl} carbamic acid tert-butyl ester → {2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-amino-phenyl)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

HRID 500102Notes

Reaction equation

HRID 500102 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([C:17](=[O:34])[NH:18][CH:19]([C:30](=[O:33])[NH:31][CH3:32])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([C:17](=[O:34])[NH:18][CH:19]([C:30](=[O:33])[NH:31][CH3:32])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68657947{2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-nitro-phenyl)-ethylcarbamoyl]-ethyl} carbamic acid tert-butyl ester

Product 1

HCID 68657871{2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-amino-phenyl)-ethylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{2-(4-Hydroxy-phenyl)-1-[1-methylcarbamoyl-2-(4-nitro-phenyl)-ethylcarbamoyl]-ethyl}carbamic acid tert-butyl ester (300, 0.617 mmol) is dissolved in methanol (10 mL). To this was added palladium on carbon (10% by weight, 100 mg). The reaction is placed under a hydrogen atmosphere until reaction is complete (tlc). The catalyst is removed by filtration and the filtrate is concentrated to provide the amine, which is used without purification.

Workup

  1. customThe reaction is placed under a hydrogen atmosphere until reaction
  2. customThe catalyst is removed by filtration
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-0d09edfc7d5a45708ad6f556debc364c
Source dataset
uspto-grants-2010_08
Patent number
US07769575B2

Reaction notes

Loading…