HCID 90051995, compound → HCID 90052007, compound

HRID 2284648Notes

Reaction equation

HRID 2284648 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=1)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[C].[Pd]>[C:14]([O:13][C:12](=[O:18])[N:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1)[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])([CH3:15])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 90051995HCID 90051995, compound

Product 1

HCID 90052007HCID 90052007, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent2×

Procedure

To a suspension of 10% palladium-carbon (500 mg) in methanol (4 mL), tert-butyl (2-((tert-butoxycarbonyl)amino)ethyl)(3-nitrophenyl)carbamate (B12, 500 mg) was added at room temperature, and the mixture was stirred at room temperature for 1 hour and 30 minutes under a hydrogen atmosphere. To the reaction mixture, methanol was added, the insoluble matter was removed by filtration through Cerite, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (eluent, 75 to 70% hexane in ethyl acetate) to obtain tert-butyl(3 -aminophenyl)(2-((tert-butoxycarbonyl)amino)ethyl)carbamate (B13, 140 mg).

Workup

  1. additionwas added at room temperature
  2. customthe insoluble matter was removed by filtration through Cerite
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by basic silica gel column chromatography (eluent, 75 to 70% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-df0437957e844d4b88daaa366ad34bba
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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