反应 #865

反应方程式

N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine

(S)-α-ethylbenzylamine

water

HOBt

→

N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide

收率 33.1%

溶剂

methylene chloride

反应条件

后处理

1. 1
   温度under cooling
2. 2
   温度under cooling
3. 3
   其他overnight
4. 4
   其他at room temperature
5. 5
   浓缩The reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate
6. 6
   workup.ADDITIONwas added
7. 7
   洗涤The resulting residue was washed two times each with 70 ml of aqueous 5% citric acid
8. 8
   干燥The resulting organic layer was dried with anhydrous magnesium sulfate
9. 9
   其他the magnesium sulfate was removed by filtration
10. 10
    浓缩the resulting filtrate was concentrated under reduced pressure
11. 11
    workup.DISSOLUTIONThe resulting residue was dissolved in chloroform
12. 12
    浓缩concentrated under reduced pressure
13. 13
    洗涤The resulting solid residue was washed with ethyl acetate
14. 14
    其他dried

实验过程

To a solution of 6.69 g (14.2 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine and 2.04 g (15.1 mmols) of (S)-α-ethylbenzylamine in 200 ml of methylene chloride were added 2.73 g (14.2 mmols) of water-soluble carbodiimide hydrochloride and 1.92 g (14.2 mmols) of HOBt under cooling and stirred for one hour under cooling and then overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate was added. The resulting residue was washed two times each with 70 ml of aqueous 5% citric acid, once with 70 ml of water, two times each with 70 ml of aqueous 5% sodium hydrogencarbonate and once with 70 ml of brine in that order. The resulting organic layer was dried with anhydrous magnesium sulfate, the magnesium sulfate was removed by filtration, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was dissolved in chloroform and concentrated under reduced pressure. The resulting solid residue was washed with ethyl acetate and dried to obtain 2.81 g (4.7 mmols) of N-benzyloxycarbonyl-β-benzyl-L-aspartyl-D-isoleucine (S)-α-ethylbenzylamide.

来源