Methanol → (R)-2-[4-(3-Fluorobenzyloxy)benzylideneamino]propanamide
Reaktionsgleichung
Cl.[NH2:2][C@@H:3]([C:5]([NH2:7])=[O:6])[CH3:4].CO.[F:10][C:11]1[CH:12]=[C:13]([CH:24]=[CH:25][CH:26]=1)[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>C(N(CC)CC)C>[F:10][C:11]1[CH:12]=[C:13]([CH:24]=[CH:25][CH:26]=1)[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[N:2][C@H:3]([CH3:4])[C:5]([NH2:7])=[O:6])=[CH:18][CH:17]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
In a 250 mL, 4 necked round bottom flask, equipped with mechanical stirrer, thermometer, reflux condenser and under a flow of nitrogen, D-alaninamide hydrochloride (6.1 g) and methanol (80 mL) are charged and stirred for 15 min at 20° C. Triethylamine (5 g) is added at such a rate that the temperature remains below 30° C. The mixture is stirred for 10 min, whereupon solid 4-(3-fluorobenzyloxy)benzaldehyde (10 g, Example 10b) is added portion wise in about 30 min. After stirring for 3 hours at 20° C., the mixture is cooled to 5° C. After stirring for 3 hours at this temperature, the solid is filtered and washed with small amount of pre-cooled methanol. The wet solid is dried under vacuum for 12 hours a 25° C., yielding 6.4 g of title compound as white solid, with 46.4% yield; m.p 111.9.
Aufarbeitung
- customIn a 250 mL, 4 necked round bottom flask, equipped with mechanical stirrer
- temperaturethermometer, reflux condenser
- customremains below 30° C
- additionis added portion wise in about 30 min
- stirringAfter stirring for 3 hours at 20° C.
- temperaturethe mixture is cooled to 5° C
- stirringAfter stirring for 3 hours at this temperature
- filtrationthe solid is filtered
- washwashed with small amount of pre-cooled methanol
- customThe wet solid is dried under vacuum for 12 hours a 25° C.
Quellen und Nachweise
- ORD-Eintrag
- ord-5820c3f822c94d19be155428f632981c
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08846763B2
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