当前位置: X-MOL 学术Org. Process Res. Dev. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
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
Organic Process Research & Development ( IF 3.4 ) Pub Date : 2018-11-05 00:00:00 , DOI: 10.1021/acs.oprd.8b00173
Tao Wang 1, 2 , Liang-Dong Du 3 , Ding-jian Wan 3 , Xiang Li 3 , Xin-Zhi Chen 2 , Guo-Feng Wu 1
Affiliation  

Here we describe an efficient and cost-effective chemoenzymatic synthesis of the β-lactamase inhibitor avibactam starting from commercially available ethyl 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)-ethyl 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.

中文翻译:

脂肪酶催化拆分在制备(2 S,5 R)-5-(苯甲氧基)氨基)哌啶-2-羧酸乙酯中的应用,β-内酰胺酶抑制剂阿维巴坦的关键中间体

在这里,我们描述了从商业上可获得的5-羟基吡啶甲酸乙酯盐酸盐开始的β-内酰胺酶抑制剂阿维巴坦的高效化学合成方法。阿维巴坦分十步合成,总收率23.9%。合成路线的特点是在制备(2 S,5 S)-5-羟基哌啶-2-羧酸乙酯(关键中间体乙基(2 S,5 R)-5-的有价值的前体)过程中新的脂肪酶催化的拆分步骤((苄氧基)氨基)哌啶-2-羧酸酯。我们的合成路线用于生产400克阿维巴坦钠盐。
更新日期:2018-11-05
down
wechat
bug