Safety of (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxamide. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxamide, is researched, Molecular C13H19N3O2, CAS is 1416134-49-0, about Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2S,5R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam. Author is Wang, Tao; Du, Liang-Dong; Wan, Ding-jian; Li, Xiang; Chen, Xin-Zhi; Wu, Guo-Feng.
Here we describe an efficient and cost-effective chemoenzymic synthesis of the β-lactamase inhibitor avibactam starting from com. available Et 5-hydroxypicolinate hydrochloride. Avibactam was synthesized in 10 steps with an overall yield of 23.9%. The synthetic route features a novel lipase-catalyzed resolution step during the preparation of (2S,5S)-Et 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate Et (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.
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Reference:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica