1224174-07-5Relevant articles and documents
Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir
Xu, Feng,Zhong, Yong-Li,Li, Hongming,Qi, Ji,Desmond, Richard,Song, Zhiguo J.,Park, Jeonghan,Wang, Tao,Truppo, Matthew,Humphrey, Guy R.,Ruck, Rebecca T.
, p. 5880 - 5883 (2017)
A practical and asymmetric synthesis of a functionalized trans-cyclopropoxy building block for the preparation of the HCV NS3/4a protease inhibitor grazoprevir is reported. Intramolecular SN2 displacement-ring closure, followed by a Baeyer-Villiger oxidation, yields the desired trans-cyclopropanol with full control of diastereoselectivity. A terminal alkyne is then effectively installed using LiNH(CH2)2NEt2. Starting from (S)-epichlorohydrin, the cyclopropoxy building block is prepared in 51% overall yield with >99.8% optical purity without isolation of any intermediates.
METHODS AND INTERMEDIATES FOR PREPARING MACROLACTAMS
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Page/Page column 24, (2015/05/05)
The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. HCV NS3 inhibitory compounds have therapeutic and research applications.