Reaktion #68708

Reaktionsgleichung

NaOH

D-alanine

NaOH

MeOC(O)Cl

→

N-methoxycarbonyl-D-alanine

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring at room temperature for 1 hour
2. 2
   Waschenthe mixture is washed with ether (3×50 mL)
3. 3
   Extraktionextracted with EtOAc (5×50 mL)
4. 4
   ExtraktionThe organic extract
5. 5
   Waschenis washed with water, brine
6. 6
   Trocknendried (MgSO4)
7. 7
   SonstigeThe solvent is removed

Vorschrift

To a solution of D-alanine (5 g, 56.1 mmol) in 1 N NaOH (152 mL, 152 mmol) at 0° C. is added a solution of MeOC(O)Cl (6.5 mL, 84.2 mmol) in diethyl ether (30 mL). The mixture is stirred in ice bath for 3 hours and then adjusted to pH 9 with 1 N NaOH. After stirring at room temperature for 1 hour, the mixture is washed with ether (3×50 mL), acidified to pH ˜2 with 5 N HCl, extracted with EtOAc (5×50 mL). The organic extract is washed with water, brine, and then dried (MgSO4). The solvent is removed to yield compound cxxxiv, N-methoxycarbonyl-D-alanine, as colorless oil (6.48 g, 79%).

Quelle