Reaktion #11021

Reaktionsgleichung

hydrochloric acid

(2S)-2-hydroxy-3-phenylpropionic acid

thionyl chloride

dimethylformamide

→

(2R)-2-chloro-3-phenylpropionic acid

Ausbeute 84.1%

Lösungsmittel

water

1,4-Dioxane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe mixture was stirred at 40° C. for 6 hours
3. 3
   TemperaturThis reaction mixture was cooled
4. 4
   Temperaturwhile maintaining the temperature at 20° C.
5. 5
   workup.STIRRINGof stirring
6. 6
   Extraktionthe mixture was extracted with 200 ml of toluene
7. 7
   workup.ADDITIONWater (70 ml) was added to the organic phase
8. 8
   Sonstigeafter pH adjustment to 9.0 with a 30% aqueous solution of sodium hydroxide, the organic phase was removed by phase separation
9. 9
   SonstigeTo the aqueous phase obtained
10. 10
    Sonstigethe aqueous phase was removed by phase separation
11. 11
    workup.DISTILLATIONThe toluene was distilled off under reduced pressure from the thus-obtained toluene phase

Vorschrift

1,4-Dioxane (200 ml) was added to 20.4 g (122.8 mmol) of (2S)-2-hydroxy-3-phenylpropionic acid (optical purity 100% ee (S)), 43.8 g (368.4 mmol) of thionyl chloride was added dropwise, and the mixture was stirred at 40° C. for 2 hours. To that solution was added 1.8 g (24.6 mmol) of dimethylformamide, and the mixture was stirred at 40° C. for 6 hours. This reaction mixture was cooled and, while maintaining the temperature at 20° C., 70 ml of water was added dropwise and, after about an hour of stirring, the mixture was extracted with 200 ml of toluene. Water (70 ml) was added to the organic phase and, after pH adjustment to 9.0 with a 30% aqueous solution of sodium hydroxide, the organic phase was removed by phase separation. To the aqueous phase obtained was added 200 ml of toluene, the pH was adjusted to 1.0 with 35% aqueous hydrochloric acid, and the aqueous phase was removed by phase separation. The toluene was distilled off under reduced pressure from the thus-obtained toluene phase to give 19.1 g (103.3 mmol, yield 84%) of (2R)-2-chloro-3-phenylpropionic acid. The optical purity of the product as determined by the same method as in Example 12 was 99.7% ee (R) (rate of configurational inversion 99.7%).

Quelle