Reacción #11010

Ecuación de reacción

sodium nitrite

L-Phenylalanine

sulfuric acid

→

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

Rendimiento 123.5%

Disolventes

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added over 5 hours
2. 2
   workup.ADDITIONAfter addition
3. 3
   ExtracciónThe combined extract (115.8 g)
4. 4
   Otroobtained

Procedimiento

L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 4.15 g (42.4 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 20° C., a mixture of 10.45 g (151.5 mmol) of sodium nitrite and 20 g of water was added over 5 hours. After addition, the mixture was further stirred at 20° C. for 20 hours and, thereafter, the same work-up procedure as in Example 1 was followed. The combined extract (115.8 g) obtained contained 8.7 g of (2S)-2-hydroxy-3-phenylpropionic acid (yield 87%, optical purity 92.0% ee). The proton concentration (normality) in the reaction of this example was 0.8 mol/kg, the amount of the protonic acid was 1.4 equivalents (relative to L-phenylalanine), and the reaction temperature was 20° C.

Fuente