反応 #84041

反応方程式

Methyl chloroformate

NaOH

L-Threonine

sodium carbonate

→

foam

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

反応条件

後処理

1. 1
   その他reach room temperature
2. 2
   洗浄The reaction mixture is washed with CH2Cl2 (3×50 mL)
3. 3
   その他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
   その他is brought to room temperature
7. 7
   その他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
   ろ過filtered
10. 10
    洗浄washed with 2:1 mixture of MeOH/CH2Cl2 (50 mL)
11. 11
    濃縮The filtrate was concentrated
12. 12
    その他dried in vacuum at 40° C.

実験手順

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%).

出典