Reaktionsgleichung
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[CH3:15][C:16]1[N:21]=[CH:20][C:19]([C:22]([OH:24])=O)=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[C:22]([C:19]1[CH:20]=[N:21][C:16]([CH3:15])=[CH:17][CH:18]=1)=[O:24]Komponenten
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 1,1-dimethylethyl (3S)-3-methyl-1-piperazinecarboxylate (1 g, 4.99 mmol) in DMF (5 ml) was added 6-methyl-3-pyridinecarboxylic acid (0.685 g, 0.340 mmol), HOBT.H2O (0.765 g, 4.99 mmol) and HBTU (1.894 g, 4.99 mmol). Finally DIPEA (2.62 ml, 14.98 mmol) was added and the reaction mixture was stirred at room temperature for 20 hours. Solvent was removed by evaporation and EtOAc was added to the residue and the solution was extracted with saturated aqueous sodium bicarbonate and sodium chloride solutions. The organic layer was evaporated to dryness and dissolved in dioxane (100 ml) and stirred with 4M HCl in dioxane (15 ml) and water (0.25 ml) overnight. The solution was evaporated to dryness and purified using an ion exchange column (SCX, Biotage) to give the title compound as an oil (1.04 g)
Aufarbeitung
- customSolvent was removed by evaporation and EtOAc
- additionwas added to the residue
- extractionthe solution was extracted with saturated aqueous sodium bicarbonate and sodium chloride solutions
- customThe organic layer was evaporated to dryness
- dissolutiondissolved in dioxane (100 ml)
- stirringstirred with 4M HCl in dioxane (15 ml) and water (0.25 ml) overnight
- customThe solution was evaporated to dryness
- custompurified
Quellen und Nachweise
- ORD-Eintrag
- ord-72d4c1c2e2d642058b9a80973bd0f26e
- Quelldatensatz
- uspto-grants-2013_09
- Patentnummer
- US08536183B2
Verknüpfte Notizen
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