The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide
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...
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crwiley:10.1002/chir.23016 2024-09-15T17:46:27+00:00 The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide Zhang, Yinjun Cheng, Feifei Yan, Hongde Zheng, Jianyong Wang, Zhao Natural Science Foundation of Zhejiang Province 2018 http://dx.doi.org/10.1002/chir.23016 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.23016 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.23016 en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor Chirality volume 30, issue 11, page 1225-1232 ISSN 0899-0042 1520-636X journal-article 2018 crwiley https://doi.org/10.1002/chir.23016 2024-08-09T04:23:34Z 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. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library Chirality 30 11 1225 1232 |
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Wiley Online Library |
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English |
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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. |
author2 |
Natural Science Foundation of Zhejiang Province |
format |
Article in Journal/Newspaper |
author |
Zhang, Yinjun Cheng, Feifei Yan, Hongde Zheng, Jianyong Wang, Zhao |
spellingShingle |
Zhang, Yinjun Cheng, Feifei Yan, Hongde Zheng, Jianyong Wang, Zhao The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide |
author_facet |
Zhang, Yinjun Cheng, Feifei Yan, Hongde Zheng, Jianyong Wang, Zhao |
author_sort |
Zhang, Yinjun |
title |
The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide |
title_short |
The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide |
title_full |
The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide |
title_fullStr |
The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide |
title_full_unstemmed |
The enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by Novozym 435 to prepare a novel triazolopyrimidine herbicide |
title_sort |
enzymatic resolution of 1‐(4‐chlorophenyl)ethylamine by novozym 435 to prepare a novel triazolopyrimidine herbicide |
publisher |
Wiley |
publishDate |
2018 |
url |
http://dx.doi.org/10.1002/chir.23016 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchir.23016 https://onlinelibrary.wiley.com/doi/pdf/10.1002/chir.23016 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Chirality volume 30, issue 11, page 1225-1232 ISSN 0899-0042 1520-636X |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/chir.23016 |
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Chirality |
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30 |
container_issue |
11 |
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1225 |
op_container_end_page |
1232 |
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1810494594511536128 |