Ethyl 4-(5-tert-butoxycarbonylaminomethyl-2-nitrophenyl)-2-ethoxycarbonylbutanoate → 2-(3,3-Diethoxycarbonylpropyl)-4-tert-butoxycarbonylaminomethylaniline

HRID 862602Notes

Reaction equation

HRID 862602 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:29]([O-])=O)=[C:14]([CH2:16][CH2:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:27]([O:26][C:24]([CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH2:16][C:14]1[CH:15]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:11]=[CH:12][C:13]=1[NH2:29])=[O:25])[CH3:28]

Participants

5

Reactant 2

HCID 19698384Ethyl 4-(5-tert-butoxycarbonylaminomethyl-2-nitrophenyl)-2-ethoxycarbonylbutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 196983562-(3,3-Diethoxycarbonylpropyl)-4-tert-butoxycarbonylaminomethylanilineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-(5-tert-butoxycarbonylaminomethyl-2-nitrophenyl)-2-ethoxycarbonylbutanoate (3.2 g, 7.3 mmol) in ethyl acetate (30 mL) was hydrogenated over palladium/charcoal (500 mg) under atmospheric pressure of hydrogen at room temperature for 2.5 h. The mixture was passed through celite and the filtrate was concentrated to give 2.8 g of the title compound (94%).

Workup

  1. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f9b375f800ca443185a5967473b355a3
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

Loading…