Reaktionsgleichung
C([O:3][C:4](=O)[C@@H:5]([N:7]([CH2:21][CH3:22])[C:8]1[C:17]([N+:18]([O-])=O)=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:9]=1)[CH3:6])C.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH2:21]([N:7]1[C@@H:5]([CH3:6])[C:4](=[O:3])[NH:18][C:17]2[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[N:9][C:8]1=2)[CH3:22]Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
(S)-methyl 6-((1-ethoxy-1-oxopropan-2-yl)(ethyl)amino)-5-nitronicotinate (1.22 g, 3.92 mmol) was dissolved in dichloromethane (12 mL). To this solution were added triphenyl phosphite (5.0 mg, 16 umol), ammonium metavanadate (50.0 mg, 0.427 mmol) and Pt/C (5% wt., 0.200 g). The reaction mixture was hydrogenated at 100 psi at 25° C. for 18 h. The mixture was filtered through a small pad of celite and the pad was washed with dichloromethane (20 mL). The combined filtrates were concentrated in vacuo and crystallized with ethyl ether (50 mL) to afford the title compound as a white solid (0.560 g, 57%). [M+H] calc'd for C12H5N3O3, 250; found, 250.
Aufarbeitung
- filtrationThe mixture was filtered through a small pad of celite
- washthe pad was washed with dichloromethane (20 mL)
- concentrationThe combined filtrates were concentrated in vacuo
- customcrystallized with ethyl ether (50 mL)
Quellen und Nachweise
- ORD-Eintrag
- ord-57f4d8d1afb74920ba819c3ef1cde15a
- Quelldatensatz
- uspto-grants-2011_04
- Patentnummer
- US07928105B2
Verknüpfte Notizen
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