반응 #5820

반응 방정식

N-(tert-butoxycarbonyl)tyrosine

N-phenylpiperazine

N-hydroxybenzotriazole

DCC

→

title compound

수율 134.2%

1-[N-(Tert-Butoxycarbonyl)Tyrosyl]-4-Phenylpiperazine

수율 134.2%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered
2. 2
   기타to remove insoluble matter, which
3. 3
   세척was then washed with 300 ml of ethyl acetate
4. 4
   농축concentrated under a reduced pressure
5. 5
   workup.DISSOLUTIONThe resulting residue was dissolved in 500 ml of ethyl acetate
6. 6
   세척the solution was washed three times with saturated sodium bicarbonate aqueous solution
7. 7
   건조once with saturated sodium chloride aqueous solution, dried over magnesium sulfate
8. 8
   농축concentrated under a reduced pressure
9. 9
   세척eluted with ethyl acetate/hexane (1:2 to 1:1)
10. 10
    기타to collect desired fractions, which
11. 11
    농축concentrated under a reduced pressure
12. 12
    workup.DISSOLUTIONResulting residue was dissolved in 100 ml of ethyl acetate
13. 13
    workup.WAITto stand overnight in a refrigerator
14. 14
    여과filtered
15. 15
    기타to remove insoluble matter
16. 16
    농축The filtrate was concentrated under a reduced pressure
17. 17
    workup.DISTILLATIONsubjected to azeatropic distillation with benzene
18. 18
    기타dried under a reduced pressure

실험 절차

19.7 g of N-(tert-butoxycarbonyl)tyrosine, 12.5 g of N-phenylpiperazine and 16.1 g of N-hydroxybenzotriazole were dissolved in 100 ml of tetrahydrofuran, and to the solution was added dropwise a solution of 18.7 g of DCC in 50 ml of tetrahydrofuran for 20 minutes with ice cooling, and the mixture was stirred for one hour. The reaction mixture was filtered to remove insoluble matter, which was then washed with 300 ml of ethyl acetate, and the filtrates were combined and concentrated under a reduced pressure. The resulting residue was dissolved in 500 ml of ethyl acetate, and the solution was washed three times with saturated sodium bicarbonate aqueous solution and once with saturated sodium chloride aqueous solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting residue was applied to a silica gel column and eluted with ethyl acetate/hexane (1:2 to 1:1) to collect desired fractions, which were then combined and concentrated under a reduced pressure. Resulting residue was dissolved in 100 ml of ethyl acetate, and the solution was allowed to stand overnight in a refrigerator and then filtered to remove insoluble matter. The filtrate was concentrated under a reduced pressure, subjected to azeatropic distillation with benzene and dried under a reduced pressure to obtain 40.0 g of the title compound in a colorless amorphous form.

출처