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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 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.

amide formation; chemoenzymatic synthesis; coupling reagents; enzyme catalysis; oxime protecting groups

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