반응 #11012

반응 방정식

sodium nitrite

L-Phenylalanine

sulfuric acid

→

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

수율 70.0%

용매

water

water

반응 조건

후처리

1. 1
   workup.ADDITIONwas added over 5 hours
2. 2
   workup.ADDITIONAfter addition
3. 3
   추출The combined extract (113.7 g)
4. 4
   기타obtained

실험 절차

L-Phenylalanine (10.00 g, 60.5 mmol) was added to a dilution of 8.88 g (90.5 mmol) of concentrated sulfuric acid in 110 g of water and then, at an inside temperature of 0° 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 0° C. for 20 hours and, thereafter, the same work-up procedure as in Example 1 was followed. The combined extract (113.7 g) obtained contained 7.0 g of (2S)-2-hydroxy-3-phenylpropionic acid (yield 70%, optical purity 96.6% ee). The proton concentration (normality) in the reaction of this example was 1.7 mol/kg, the amount of the protonic acid was 3.0 equivalents (relative to L-phenylalanine) and the reaction temperature was 0° C.

출처