公开(公告)号：US20150315145A1

公开(公告)日：2015-11-05

申请号：US14440196

申请日：2013-10-25

Applicant: KANEKA CORPORATION

Inventor： Yoshinori HIRAI ,  Akira NISHIYAMA

IPC: C07D211/98 ,  C07D471/18

CPC classification number: C07D211/98 ,  C07B53/00 ,  C07D211/60 ,  C07D471/08 ,  C07D471/18 ,  C07D487/08

Abstract: A problem to be solved by the present invention is to provide a process for producing an optically active bicyclic urea compound useful as an intermediate for β-lactamase inhibitor, in a simple and easy manner with high efficiency.The present invention includes reacting a specific ester compound with a specific amine in the presence of a metal alkoxide and/or an alkaline earth metal salt to produce the corresponding amide compound, which is then reacted with phosgene or a phosgene equivalent, followed by, if necessary, treatment with an acid or a base, to produce an optically active bicyclic urea compound. This makes it possible to produce an optically active bicyclic urea compound in a simple and easy manner with high efficiency and in high optical purity, without using expensive reagents such as catalysts and condensation agents, and without passing through protection and deprotection steps.

Abstract translation: 本发明要解决的问题是提供以简单且容易的方式高效率地制备用作β-内酰胺酶抑制剂的中间体的光学双环脲化合物的方法。 本发明包括在金属醇盐和/或碱土金属盐的存在下使特定的酯化合物与特定的胺反应以产生相应的酰胺化合物，然后与光气或光气当量反应，然后如果 必需的，用酸或碱处理，以产生光学双环脲化合物。 这使得可以以简单和容易的方式以高效率和高光学纯度生产光学活性双环脲化合物，而不使用昂贵的试剂如催化剂和缩合剂，并且不经过保护和脱保护步骤。