Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate → Methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate

HRID 1160999

Reaktionsgleichung

Reaktionsgleichung von HRID 1160999
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[N+:23]([O-])=O)[C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[NH2:23][C:22]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Komponenten

4

Edukt 1

HCID 67235341Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate

Produkt 1

HCID 11962077Methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21584119Ethylacetate methanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Methyl 3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)-4-nitrobenzoate (10.2 g) in solution in a mixture of ethyl acetate/methanol 3:1 (300 ml), and 10% palladium on carbon (1.02 g) are introduced into an autoclave. After stirring for 4 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 (7.75 g; 83% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e86b4ef854a140079e521ae51ca7627a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816539B2

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