1192651-80-1Relevant articles and documents
Recovery and preparation method of avibactam sodium
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Paragraph 0048-0049, (2020/06/09)
The invention belongs to the technical field of medical chemistry, and particularly relates to a method for recycling, purifying and preparing a beta-lactamase inhibitor drug avibactam sodium. The method for recycling and preparing the sterile powder product is simple to operate and mild in condition, avoids hydrogenation catalytic operation for preparing a compound II from a starting material, reduces the safety risk, greatly improves the product purity, and is suitable for large-scale production.
Simple and convenient production method of avibactam
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, (2019/07/16)
The invention provides a simple and convenient production method of avibactam. The simple and convenient production method of the avibactam comprises the steps of using piperidyl-5-keto-2S-formate IIas a raw material, making the piperidyl-5-keto-2S-formate II and O-protecting group hydroxylamine hydrochloride subjected to condensation reaction, and then obtaining 5R-substituted oxyaminopiperidyl-2S-formic acid V through reduction, chiral resolution and hydrolysis under an alkaline condition; and then making the 5R-substituted oxyamino piperidyl-2S-formic acid V and phosgene or triphosgene ordiphosgene subjected to cyclic urea reaction reaction, acylating chlorination reaction and amidation reaction through a one-pot method, obtaining {[(2S,5R)-2-formamyl-7-oxo-1,6-diazetidine[3.2.1]octane-6-yl]oxy}sulfonyl tetra-n-butylammonium salt VII through protecting group take-off, sulphating and tetrabutyl amination salification, and producing the avibactam I finally through ion exchange. Thesimple and convenient production method of the avibactam is simple and convenient in production route, easy to operate, low in raw material price, low in cost, small in three waste discharge, high inatom utilization rate, economical and environmentally friendly, and the yields of the various steps are high, so that the simple and convenient production method of the avibactam benefits industrial production of the avibactam.
RETRACTED ARTICLE: A New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation
Wang, Tao,Du, Liang-Dong,Wan, Ding-Jian,Li, Xiang,Chen, Xin-Zhi,Wu, Guo-Feng
, p. 267 - 272 (2018/03/22)
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.