An efficient synthesis of avibactam starting from commercially available ethyl-5-hydroxypicolinate was completed in 10 steps and 23.9% overall yield. The synthesis features a novel lipase-catalyzed resolution, in the preparation of (2S,5S)-5-hydroxypiperidine-2-carboxylate acid, which is a valuable precusor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. An optimized one-pot debenzylation/sulfation reaction, followed by cation exchange, gave the avibactam sodium salt on a 400.0 g scale.

中文翻译：

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一种新的合成阿维巴坦的途径：脂肪酶催化拆分和同时脱苄基/硫酸化。

由市售的5-羟基吡啶甲酸乙酯开始的高效合成avibactam的过程分为10个步骤，总产率为23.9％。在制备（2 S，5 S）-5-羟基哌啶-2-羧酸（2 S，5 S）-5-羟基哌啶-2-羧酸的过程中，该合成具有新颖的脂肪酶催化拆分作用，这是关键的中间体乙基（2 S，5 R）-5的有价值的先驱-（（苄氧基）氨基）哌啶-2-羧酸酯。经过优化的一锅脱苄基/硫酸化反应，然后进行阳离子交换，得到了400.0克规模的阿维巴坦钠盐。