Enzyme-catalyzed cascade synthesis of hydroxyiminoacetamides

In order to synthesize N-(3-azido-1- phenylpropyl)-2-hydroxyiminoacetamide, a key compound for the preparation of acetylcholinesterase (AChE) reactivators of the N- substituted 2-hydroxyiminoacetamide type, it was necessary to develop a method for forming an amide bond between an ethyl glyoxylate ox...

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Bibliographic Details
Main Authors: Knežević, Anamarija, Vinković, Vladimir, Maraković, Nikola, Šinko, Goran
Format: Article in Journal/Newspaper
Language:Croatian
Published: Elsevier 2014
Subjects:
Online Access:http://fulir.irb.hr/3660/
http://fulir.irb.hr/3660/1/Tetr%20Lett%20postprint.pdf
http://www.sciencedirect.com/science/article/pii/S0040403914010065
https://doi.org/10.1016/j.tetlet.2014.06.027
Description
Summary:In order to synthesize N-(3-azido-1- phenylpropyl)-2-hydroxyiminoacetamide, a key compound for the preparation of acetylcholinesterase (AChE) reactivators of the N- substituted 2-hydroxyiminoacetamide type, it was necessary to develop a method for forming an amide bond between an ethyl glyoxylate oxime and an amine. Using Candida antarctica lipase B (CAL-B) in a cascade enzyme-BOP catalyzed reaction, the efficient synthesis of the target hydroxyiminoacetamide was achieved.