반응 #3766

반응 방정식

acetic acid

triethylamine

diphenyl chlorophosphate

N-hydroxysuccinimide

→

acetic acid succinimidyl ester

수율 70.0%

용매

ethyl acetate

ethyl acetate

ethyl acetate

ethyl acetate

반응 조건

후처리

1. 1
   기타rising to 41° C
2. 2
   기타A thick, white suspension resulted
3. 3
   온도heated at 45°-55° C. for 16 hours
4. 4
   기타After ending of the reaction
5. 5
   여과the solid was filtered off
6. 6
   세척washed with 2×3 ml of ethyl acetate
7. 7
   기타The combined filtrates were evaporated in vacuo
8. 8
   세척the semicrystalline residue which remained was washed
9. 9
   기타The white solid thus obtained
10. 10
    여과was filtered off
11. 11
    세척washed with 2×3 ml of ethanol
12. 12
    기타sucked dry
13. 13
    세척washed
14. 14
    workup.STIRRINGby stirring with 10 ml of isopropanol
15. 15
    여과After filtering off
16. 16
    세척washing with 2×2 ml of isopropanol
17. 17
    기타drying in vacuo

실험 절차

1.27 g (0.011 mol) of N-hydroxysuccinimide were initially introduced into 10 ml of ethyl acetate, a solution of 3.22 g (0.012 mol) of diphenyl chlorophosphate in 10 ml of ethyl acetate was added and then a solution of 2.53 g (0.025 mol) of triethylamine in 10 ml of ethyl acetate was added dropwise in the course of 10 minutes, the temperature rising to 41° C. A thick, white suspension resulted, which was treated with a solution of 0.6 g (0.01 mol) of acetic acid in 10 ml of ethyl acetate and heated at 45°-55° C. for 16 hours. After ending of the reaction, the solid was filtered off and washed with 2×3 ml of ethyl acetate. The combined filtrates were evaporated in vacuo and the semicrystalline residue which remained was washed by stirring with 20 ml of ethanol for 30 minutes. The white solid thus obtained was filtered off, washed with 2×3 ml of ethanol, sucked dry and then washed by stirring with 10 ml of isopropanol. After filtering off, washing with 2×2 ml of isopropanol and drying in vacuo, 1.1 g (70%) of white acetic acid succinimidyl ester were obtained.

출처