Acetic Acid → Acetic acid N-hydroxysuccinimide ester

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.

1. customrising to 41° C
2. customA thick, white suspension resulted
3. temperatureheated at 45°-55° C. for 16 hours
4. customAfter ending of the reaction
5. filtrationthe solid was filtered off
6. washwashed with 2×3 ml of ethyl acetate
7. customThe combined filtrates were evaporated in vacuo
8. washthe semicrystalline residue which remained was washed
9. customThe white solid thus obtained
10. filtrationwas filtered off
11. washwashed with 2×3 ml of ethanol
12. customsucked dry
13. washwashed
14. stirringby stirring with 10 ml of isopropanol
15. filtrationAfter filtering off
16. washwashing with 2×2 ml of isopropanol
17. customdrying in vacuo

ORDレコード

ord-46ef6b3fdcb74f75b3a22e357525e9cd

出典データセット

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05734064