N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate → t-Butyl N-[2-amino-5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)phenyl]-N-methylcarbamate

HRID 2303856Notes

Reaction equation

HRID 2303856 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:29]([CH3:30])=[CH:28][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([N+:25]([O-])=O)=[C:18]([N:20]([CH3:24])[C:21](=[O:23])[O-:22])[CH:19]=2)=[CH:11][C:10]=1[CH3:31])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:25][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:12]2[CH:28]=[C:29]([CH3:30])[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[C:10]([CH3:31])[CH:11]=2)=[CH:19][C:18]=1[N:20]([CH3:24])[C:21](=[O:23])[O:22][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69820678N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate

Product 1

HCID 18184919t-Butyl N-[2-amino-5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)phenyl]-N-methylcarbamateYield 171.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.71 g of N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate, 0.2 g of 10% palladium on carbon and 100 ml of methanol was stirred vigorously at room temperature for 11 hours under a hydrogen atmosphere. The catalyst was filtered off from the reaction mixture and the filtrate was concentrated by evaporation, whereby 1.56 g of the title compound were obtained.

Workup

  1. filtrationThe catalyst was filtered off from the reaction mixture
  2. concentrationthe filtrate was concentrated by evaporation

Sources & evidence

ORD record
ord-4647305545cf4fd6b98f0aa89173c492
Source dataset
uspto-grants-2002_08
Patent number
US06432993B1

Reaction notes

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