Reaktionsgleichung
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH2:11][C@@H:12]([C:16]([OH:18])=[O:17])[C@H:13]([CH3:15])[OH:14].C([O-])([O-])=O.[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([NH:11][C@H:12]([C@@H:13]([OH:14])[CH3:15])[C:16]([OH:18])=[O:17])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]Komponenten
Reaktionsbedingungen
- Temperatur
- 75 °C
Versuchsvorschrift
2-chloro-4-fluorobenzonitrile (60702-69-4) (2.0 g, 12.86 mmol) was mixed together with H-D-Thr-OH (1.84 g, 15.43 mmol) in DMSO (30 mL). K2CO3 (3.73 g, 27.0 mmol) was added to the reaction mixture and stirred at 75° C. for 24 h. The reaction mixture was cooled down to room temperature and poured slowly into a 10% citric acid solution and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times to get the crude product. The crude product was chromatographed with a gradient of hexane EtOAc and then with EtOAc, 100% to get the pure final product 1.8 g): 1H NMR (500 MHz, acetone-d6, δ in ppm) 7.51 (d, J=9 Hz, 1H), 6.95 (s, 1H), 6.82 (d, J=9 Hz, 1H), 5.17 (d, J=9 Hz, 1H), 4.42 (m, 1H), 4.22 (d, J=6 Hz, 1H), 2.34 (s, 3H), 1.28 (d, J=6 Hz, 3H).
Aufarbeitung
- temperatureThe reaction mixture was cooled down to room temperature
- stirringstirred for 10 min at room temperature
- extractionThe solution was extracted with EtOAc several times
- customto get the crude product
- customThe crude product was chromatographed with a gradient of hexane EtOAc
Quellen und Nachweise
- ORD-Eintrag
- ord-88382b334e3f4ce2b33f635e6e76605b
- Quelldatensatz
- uspto-grants-2014_01
- Patentnummer
- US08629167B2
Verknüpfte Notizen
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