Tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate → Tert-butyl 2-amino-4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)benzoate
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:31])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:27]=[CH:26][C:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:17]([N+:28]([O-])=O)[CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.CO.[C].[Pd]>[NH2:28][C:17]1[CH:16]=[C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:31])[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution mixture of tert-butyl 4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)-2-nitrobenzoate (57 mg) in ethyl acetate (2.5 mL) and methanol (2.5 mL), 10% palladium-carbon (11 mg) was added. The resulting mixture was stirred at room temperature for 3 hours under a hydrogen atmosphere. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate] to obtain 48 mg of tert-butyl 2-amino-4-(2-((tert-butoxycarbonyl)(methyl)amino)phenyl)benzoate as a white solid.
Workup
- additionwas added
- customThe insoluble substance was removed by filtration
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography [eluent: 95-85% hexane/ethyl acetate]
Sources & evidence
- ORD record
- ord-413d9799cc8d42568db2a8ec6b8f54ea
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492582B2
Reaction notes
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