تفاعل #84040

معادلة التفاعل

Methyl chloroformate

NaOH

L-Leucine

sodium carbonate

→

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

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر