(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid → (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acid

HRID 1698770

Reaktionsgleichung

Reaktionsgleichung von HRID 1698770
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 54512598(R)-2-((tert-Butoxycarbonyl)amino)-3-((2-nitrophenyl)amino)propanoic acid

Produkt 1

HCID 58595312(R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-(−)-2-tert-butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (7.6 g) in tetrahydro-furan (100mL), 10% palladium carbon (1 g) was added, followed by stirring at room temperature for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure, whereby (R)-2-tert-butoxycarbonylamino-3-(2-aminophenylamino)-propi onic acid was obtained. It was dissolved in toluene (100 mL). The solution was refluxed overnight. The reaction mixture was allowed to cool down and then concentrated under reduced pressure. The residue was purified by silica gel colomn chromatography (ethyl acetate:n-hexane=1:1), whereby the title compound (5.16 g) was obtained. Yield: 80%.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2a9a744fa0134cb6a8b2300425381b68
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344452B1

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