Tert-butyl 3-[(5-{[bis(3-methylbutyl)amino]carbonyl}-2-nitrophenyl)amino]propylcarbamate → Tert-butyl 3-[(2-amino-5-{[bis(3-methylbutyl)amino]carbonyl}phenyl)amino]propylcarbamate

HRID 899907Notes

Reaction equation

[CH3:1][CH:2]([CH3:34])[CH2:3][CH2:4][N:5]([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[C:6]([C:8]1[CH:9]=[CH:10][C:11]([N+:26]([O-])=O)=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:13]=1)=[O:7]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:26][C:11]1[CH:10]=[CH:9][C:8]([C:6]([N:5]([CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:4][CH2:3][CH:2]([CH3:34])[CH3:1])=[O:7])=[CH:13][C:12]=1[NH:14][CH2:15][CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 20 °C

Procedure

Tert-butyl 3-[(5-{[bis(3-methylbutyl)amino]carbonyl}-2-nitrophenyl)amino]propylcarbamate (1.65 g) in solution in a mixture of ethyl acetate/ethanol 2:1 (130 ml), and 10% palladium on carbon (165 mg) are introduced into an autoclave. After stirring for 3 hours under a hydrogen atmosphere (3 bar) at a temperature of approximately 20° C., the catalyst is eliminated by filtration on celite and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (1.35 g; 89% yield).

Workup

additionare introduced into an autoclave
filtrationthe catalyst is eliminated by filtration on celite
concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record: ord-fc03050bbe4e4c61a2716c9c81665cc9
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07355052B2

Reaction notes

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