反应 #84041

反应方程式

Methyl chloroformate

NaOH

L-Threonine

sodium carbonate

→

foam

(2S,3R)-3-hydroxy-2-(methoxycarbonylamino)butanoic acid

反应条件

后处理

1. 1
   其他reach room temperature
2. 2
   洗涤The reaction mixture is washed with CH2Cl2 (3×50 mL)
3. 3
   其他the aqueous layer is contained in a round bottom flask
4. 4
   温度cooled over an ice-water bath
5. 5
   workup.ADDITIONConcentrated HCl (aq) is added drop wise until pH 2
6. 6
   其他is brought to room temperature
7. 7
   其他the water is removed in vacuum
8. 8
   workup.ADDITIONThe residue was taken up in a 2:1 mixture of MeOH/CH2Cl2 (150 mL
9. 9
   过滤filtered
10. 10
    洗涤washed with 2:1 mixture of MeOH/CH2Cl2 (50 mL)
11. 11
    浓缩The filtrate was concentrated
12. 12
    其他dried in vacuum at 40° C.

实验过程

An aqueous NaOH (1 M, 167 mL) solution is added, while stirring, to L-Threonine (20 g, 30.5 mmol) in a round bottom flask (1 L). To this solution was added sodium carbonate (9.8 g, 92.3 mmol). The flask is cooled to 0° C. in an ice-water bath. Methyl chloroformate (14.3 mL, 184.7 mmol) is added drop wise and the reaction mixture is allowed to stir for 15 hours and reach room temperature. The reaction mixture is washed with CH2Cl2 (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 aqueous solution is brought to room temperature and the water is removed in vacuum. The residue was taken up in a 2:1 mixture of MeOH/CH2Cl2 (150 mL, filtered and washed with 2:1 mixture of MeOH/CH2Cl2 (50 mL). The filtrate was concentrated and dried in vacuum at 40° C., resulting in white foam (29.1 g, 98%).

来源