Potassium Fluoride → (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoro-6-methylpyrimidin-4-yl)oxazolidin-2-one
Reaktionsgleichung
[F-:1].[K+].[C:3]([O:7][C@@H:8]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18](Cl)[N:17]=1)[CH3:9])([CH3:6])([CH3:5])[CH3:4]>CS(C)=O.C(OCC)(=O)C.O>[C:3]([O:7][C@@H:8]([C@H:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[C:16]1[CH:21]=[C:20]([CH3:22])[N:19]=[C:18]([F:1])[N:17]=1)[CH3:9])([CH3:6])([CH3:5])[CH3:4]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
Potassium fluoride (0.063 g, 1.08 mmol, 10 equiv) was added to a solution of (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-chloro-6-methylpyrimidin-4-yl)oxazolidin-2-one (34 mg, 0.108 mmol) in DMSO (1.1 mL). The suspension was heated at 120° C. for 3 hours and then cooled to room temperature. The reaction was diluted with ethyl acetate (20 mL) and water (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to give crude (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoro-6-methylpyrimidin-4-yl)oxazolidin-2-one, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.99 (d, J=3.8 Hz, 1H), 4.71 (m, 1H), 4.65 (m, 1H), 4.46 (m, 1H), 4.41 (m, 1H), 2.53 (s, 3H), 1.25 (s, 9H), 1.03 (d, J=6.5 Hz, 3H); MS m/z 298.2 (M+H)+; Rt-0.96 min.
Aufarbeitung
- temperaturecooled to room temperature
- customThe layers were separated
- extractionthe aqueous layer was extracted with ethyl acetate (20 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-d407e169777347ecab5b4db92a94ab1a
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09434719B2
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