반응 #865

반응 방정식

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

(S)-α-ethylbenzylamine

water

HOBt

→

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

수율 33.1%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도under cooling
2. 2
   온도under cooling
3. 3
   기타overnight
4. 4
   기타at room temperature
5. 5
   농축The reaction mixture was concentrated under reduced pressure, and 150 ml of ethyl acetate
6. 6
   workup.ADDITIONwas added
7. 7
   세척The resulting residue was washed two times each with 70 ml of aqueous 5% citric acid
8. 8
   건조The resulting organic layer was dried with anhydrous magnesium sulfate
9. 9
   기타the magnesium sulfate was removed by filtration
10. 10
    농축the resulting filtrate was concentrated under reduced pressure
11. 11
    workup.DISSOLUTIONThe resulting residue was dissolved in chloroform
12. 12
    농축concentrated under reduced pressure
13. 13
    세척The resulting solid residue was washed with ethyl acetate
14. 14
    기타dried

실험 절차

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.

출처