Réaction #84040

Équation de réaction

Methyl chloroformate

NaOH

L-Leucine

sodium carbonate

→

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

Conditions de réaction

Traitement

1. 1
   Autrereach room temperature
2. 2
   AutreThe reaction mixture is separated with ether (3×50 mL)
3. 3
   Autrethe aqueous layer is contained in a round bottom flask
4. 4
   Températurecooled over an ice-water bath
5. 5
   workup.ADDITIONConcentrated HCl (aq) is added drop wise until pH 2
6. 6
   Autreis brought to room temperature
7. 7
   Extractionextracted with 2-Me-THF (3×50 mL)
8. 8
   Séchagedried (MgSO4)
9. 9
   Autrethe solids removed by filtration
10. 10
    Autrethe solvents of the filtrate removed under reduced pressure
11. 11
    AutreThe 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
    Autrethe solvent were removed in vacuum
14. 14
    Autreresulting in N-methoxycarbonyl-L-leucine (1.9 g, 32%)

Mode opératoire

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%).

Source