The enzymatic resolution of 1-(4-chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide

Chirality
Yinjun ZhangZhao Wang

Abstract

The kinetic resolution of (R,S)-1-(4-chlorophenyl)ethylamine was accomplished using a commercial lipase from Candida antarctica (Novozym 435). The performance of this lipase was investigated for the enantioselective amidation of (R,S)-1-(4-chlorophenyl)ethylamine, leaving the target product (S)-1-(4-chlorophenyl)ethylamine in its unreacted form. The effects of various types of solvents and an acyl donor, the molar ratio of the substrate to the acyl donor, and the reaction temperature were studied. The optimum reaction conditions were found to result in amidation with methyl 2-tetrahydrofuroate at 40°C in methyl tert-butyl ether, with a substrate/acyl donor molar ratio of 1:2.4. The conversion rate of (R,S)-1-(4-chlorophenyl)ethylamine was 52%, with an enantiomeric excess of 99% towards the unreacted substrate in a reaction time of 22 hours. Finally, using optically pure (S)-1-(4-chlorophenyl)ethylamine as the raw material, the chemical synthesis of (S)-N-(1-(4-chlorphenyl)ethyl)-2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)acetamide, a novel triazolopyrimidine herbicide, was achieved, and the total yield and purity were 83.5% and 95.3%, respectively.

References

Oct 28, 2010·Beilstein Journal of Organic Chemistry·Lisa K Thalén, Jan-E Bäckvall
Apr 6, 2013·Organic & Biomolecular Chemistry·Amanda S de MirandaRodrigo O M A de Souza
Nov 10, 2015·Biotechnology and Applied Biochemistry·Hong De YanZhao Wang
Dec 18, 2015·Enzyme and Microbial Technology·Kuan-Miao Liu, Kuan-Ju Liu
Sep 2, 2017·Enzyme and Microbial Technology·Hadjer ZaakRoberto Fernandez-Lafuente
Feb 28, 2018·Biotechnology Journal·Feng ChengTsvetan Kardashliev

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Citations

Oct 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marzena Wosińska-Hrydczuk, Jacek Skarżewski

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