(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid → tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]carbamate

HRID 1178782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178782
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-])=O)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][C:14]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:20][C:10]1=[O:11])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 2761798(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid

Produkt 1

HCID 57049298tert-Butyl [(3S)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]carbamateAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The title compound may be prepared either as described in US 2004/002495 or as follows: To a solution of (S)-2-(tert-butyloxycarbonylamino)-3-(2-nitrophenyl)propanoic acid (987 mg, 3.18 mmol, Peptech catalog # BL284) in MeOH (100 mL) was added 10% palladium on carbon (300 mg), and the mixture was stirred at RT under hydrogen at 80 psi for 24 h. Filtration and solvent evaporation under vacuum provided the title compound (800 mg) as a foam.

Aufarbeitung

  1. filtrationFiltration and solvent evaporation under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7a933dbae85c446d8e21136dadba01a5
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276608B2

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