Reaktion #81111

Reaktionsgleichung

tert-Leucine

thionyl chloride

methanol

thionyl chloride

→

title compound

Ausbeute 92.0%

L-tert-Leucine Methyl ester Hydrochloride

Ausbeute 92.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was warmed at 50° C. for 5 hours
2. 2
   Temperaturre-cooled to -20° C.
3. 3
   TemperaturThe reaction mixture was heated an additional 2.5 hours at 50° C.
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   Sonstigeto afford an amorphous solid
6. 6
   SonstigeThe solid was triturated with ether

Vorschrift

To anhydrous methanol (15 mL) at -20° C. under nitrogen was added thionyl chloride (4 mL) dropwise. The solution was allowed to warm to room temperature and then tert-Leucine (4.00 g) was added. The reaction mixture was warmed at 50° C. for 5 hours, re-cooled to -20° C. and then additional thionyl chloride (3 mL) was added dropwise. The reaction mixture was heated an additional 2.5 hours at 50° C. and then concentrated under reduced pressure and chased twice with methanol (15 mL) to afford an amorphous solid. The solid was triturated with ether to afford the title compound in 92% yield. The 300 MHz 1H NMR spectrum was found to be consistent with the proposed structure. MS (DCI/NH3) m/e 146 (M+H)+.

Quelle