Reaktion #538958

Reaktionsgleichung

(R)-2-amino-3-hydroxypropanoic acid

thionyl chloride

methanol

→

(R)-methyl 2-amino-3-hydroxypropanoate hydrochloride salt

Ausbeute 100.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Temperaturthe reaction mixture was heated
3. 3
   Temperaturat reflux for 12 h
4. 4
   SonstigeVolatiles were evaporated

Vorschrift

To a solution of (R)-2-amino-3-hydroxypropanoic acid (105 g, 1 mol) in methanol (1200 mL) was added thionyl chloride (87.6 mL, 142.8 g, 1.2 mol) dropwise at 0° C. After addition, the reaction mixture was heated at reflux for 12 h. Volatiles were evaporated to give the (R)-methyl 2-amino-3-hydroxypropanoate hydrochloride salt (155 g, yield 100%) as a solid that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 8.51 (brs, 2H), 4.08 (s, 1H), 3.79 (m, 2H), 3.71 (s, 3H).

Quelle