Reaktion #325747

Reaktionsgleichung

2-Chloro-4-fluoro-3-propylbenzonitrile

H-D-Thr-OH

K2CO3

→

crude product

Ausbeute 13.4%

(2R,3S)-2-(3-Chloro-4-cyano-2-propylphenylamino)-3-hydroxybutanoic acid

Ausbeute 13.4%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then cooled to room temperature
2. 2
   Sonstigepartitioned between water and EtOAc
3. 3
   SonstigeThe layers were separated
4. 4
   Extraktionthe aqueous extract
5. 5
   Waschenwas washed once with EtOAc
6. 6
   ExtraktionThe aqueous extract
7. 7
   workup.ADDITIONwas then acidified by slow addition of citric acid
8. 8
   workup.STIRRINGstirred for 10 min at room temperature
9. 9
   ExtraktionThe solution was extracted with EtOAc several times
10. 10
    Waschenwashed with water
11. 11
    Trocknendried over Na2SO4
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated in vacuo

Vorschrift

2-Chloro-4-fluoro-3-propylbenzonitrile (CAS 924626-89-1, 3.22 g, 16.3 mmol) was mixed together with H-D-Thr-OH (2.33 g, 19.6 mmol) in DMSO (30 mL) at room temperature. K2CO3 (4.73 g, 34.2 mmol) was added and the reaction mixture was stirred at 80° C. for 40 h. The reaction mixture was then cooled to room temperature and partitioned between water and EtOAc. The layers were separated and the aqueous extract was washed once with EtOAc. The aqueous extract was then acidified by slow addition of citric acid and stirred for 10 min at room temperature. The solution was extracted with EtOAc several times and the organic extracts were combined, washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to obtain the crude product (0.650 g, 13% yield), which was carried on to the next step without further purification.

Quelle