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

HRID 1643870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1643870
[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) 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-2d5b7fe5541c40c09d93c44770be13d7
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119808B2

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