2-[Bis[(tert-butyloxy)carbonyl]amino]-3-nitrobenzoic Acid Methyl Ester → Methyl 3-amino-2-(bis(tert-butoxycarbonyl)amino)benzoate

HRID 520444Notes

Reaction equation

HRID 520444 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:9]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Ni]>[NH2:19][C:18]1[C:9]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 113728532-[Bis[(tert-butyloxy)carbonyl]amino]-3-nitrobenzoic Acid Methyl Ester

Product 1

HCID 58552839Methyl 3-amino-2-(bis(tert-butoxycarbonyl)amino)benzoateYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Raney Ni (1 g) was added to a solution of methyl 2-(bis-(tert-butoxycarbonyl)amino)-3-nitrobenzoate 12 (6 g, 27.5 mmol) in THF. The reaction mixture was hydrogenated under balloon pressure for 4 h. The catalyst was removed by filtration and the solvent evaporated to give 13 (4.4 g, 80% yield).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-2fc75285a5d64b158ab1ce23b6b541ce
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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