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

HRID 412375Notes

Reaction equation

HRID 412375 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:33]([CH3:34])=[CH:32][C:12]([O:13][C:14]2[CH:15]=[CH:16][C:17]([N+:29]([O-])=O)=[C:18]([N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:19]=2)=[CH:11][C:10]=1[CH3:35])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:29][C:17]1[CH:16]=[CH:15][C:14]([O:13][C:12]2[CH:32]=[C:33]([CH3:34])[C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[C:10]([CH3:35])[CH:11]=2)=[CH:19][C:18]=1[N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 181849432-(N-t-Butoxycarbonyl-N-methylamino)-4-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)nitrobenzene

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-nitrophenyl]-N-methylcarbamate (1.71 g) in methanol (100 ml) was added 10% palladium on carbon (0.2 g). The mixture was vigorously stirred under a hydrogen atmosphere at room temperature for 11 hours. The catalyst was filtered off and the solvent of the filtrate was evaporated to afford the desired compound (1.56 g, Rf=0.14: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=1:3 as the eluant).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent of the filtrate was evaporated

Sources & evidence

ORD record
ord-1a82f464a7074a4996e73efb891ed7f9
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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