Reaktionsgleichung
C([O-])([O-])=O.[K+].[K+].F[C:8]1[C:16]2[CH:15]=[CH:14][S:13][C:12]=2[C:11]([C:17]#[N:18])=[CH:10][CH:9]=1.[NH2:19][C@@H:20]([C:24]([OH:26])=[O:25])[C@H:21]([CH3:23])[OH:22]>CS(C)=O>[C:17]([C:11]1[C:12]2[S:13][CH:14]=[CH:15][C:16]=2[C:8]([NH:19][C@H:20]([C@@H:21]([OH:22])[CH3:23])[C:24]([OH:26])=[O:25])=[CH:9][CH:10]=1)#[N:18]Komponenten
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
K2CO3 (1.97 g, 14.3 mmol) was added to a mixture of 4-fluorobenzo[b]thiophene-7-carbonitrile [(1.01 g, 5.70 mmol), which was prepared according to the procedures reported in WO 2004016576] and D-threonine (815 mg, 6.84 mmol) in DMSO (15 mL) at room temperature. The resulting mixture was heated to 80° C. and stirred for 15 h. After cooling to room temperature, the reaction mixture was poured into ice-water (150 mL) and extracted with 10% EtOAc in hexanes (2×50 mL). The aqueous phase was acidified to pH=2˜3 with 2N HCl and extracted with EtOAc (2×100 mL). The EtOAc extracts were washed with water, brine and dried with Na2SO4. Removal of the solvent gave the crude (2R,3S)-2-(7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoic acid (1.20 g, 76%). 1H NMR (400 MHz, Acetone-d6, δ in ppm) 7.81 (d, J=5.7 Hz, 1H), 7.73 (d, J=5.7 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 6.66 (d, J=8.4 Hz, 1H), 6.12 (d, J=8.0 Hz, 1H), 4.46 (m, 1H), 4.33 (m, 1H), 1.34 (d, J=6.2 Hz, 3H).
Aufarbeitung
- customwas prepared
- customat room temperature
- temperatureAfter cooling to room temperature
- extractionextracted with 10% EtOAc in hexanes (2×50 mL)
- extractionextracted with EtOAc (2×100 mL)
- washThe EtOAc extracts were washed with water, brine
- dry with materialdried with Na2SO4
- customRemoval of the solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-7e94225e6bc54663add0bb4e03c808f2
- Quelldatensatz
- uspto-grants-2014_01
- Patentnummer
- US08629167B2
Verknüpfte Notizen
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