Reaktion #84040

Reaktionsgleichung

Methyl chloroformate

NaOH

L-Leucine

sodium carbonate

→

(S)-2-(methoxycarbonylamino)-4-methylpentanoic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereach room temperature
2. 2
   SonstigeThe reaction mixture is separated with ether (3×50 mL)
3. 3
   Sonstigethe aqueous layer is contained in a round bottom flask
4. 4
   Temperaturcooled over an ice-water bath
5. 5
   workup.ADDITIONConcentrated HCl (aq) is added drop wise until pH 2
6. 6
   Sonstigeis brought to room temperature
7. 7
   Extraktionextracted with 2-Me-THF (3×50 mL)
8. 8
   Trocknendried (MgSO4)
9. 9
   Sonstigethe solids removed by filtration
10. 10
    Sonstigethe solvents of the filtrate removed under reduced pressure
11. 11
    SonstigeThe compound was purified by silicagel chromatography with gradient elution from CH2Cl2 to CH2Cl2/MeOH/acetic acid 17/2/1
12. 12
    workup.ADDITIONFractions containing product
13. 13
    Sonstigethe solvent were removed in vacuum
14. 14
    Sonstigeresulting in N-methoxycarbonyl-L-leucine (1.9 g, 32%)

Vorschrift

An aqueous NaOH (1M, 2.6 mL) solution is added, while stirring, to L-Leucine (4 g, 30.5 mmol) in a round bottom flask (250 mL). To this solution was added sodium carbonate (1.62 g, 15.2 mmol). The flask is cooled to 0° C. in an ice-water bath. Methyl chloroformate (2.6 mL, 33.5 mmol) is added drop wise and the reaction mixture is allowed to stir for 15 hours and reach room temperature. The reaction mixture is separated with ether (3×50 mL), and the aqueous layer is contained in a round bottom flask and cooled over an ice-water bath. Concentrated HCl (aq) is added drop wise until pH 2. The reaction mixture is brought to room temperature and extracted with 2-Me-THF (3×50 mL). The organic layers are pooled, dried (MgSO4), the solids removed by filtration, and the solvents of the filtrate removed under reduced pressure. The compound was purified by silicagel chromatography with gradient elution from CH2Cl2 to CH2Cl2/MeOH/acetic acid 17/2/1. Fractions containing product were combined and the solvent were removed in vacuum, resulting in N-methoxycarbonyl-L-leucine (1.9 g, 32%).

Quelle