1426573-07-0Relevant articles and documents
Diastereoselective FeCl3·6H2O/NaBH4 Reduction of Oxime Ether for the Synthesis of β-Lactamase Inhibitor Relebactam
Chen, Qinghao,Chung, John Y. L.,Dumas, Aaron,Gudipati, Venugopal,Lam, Yu-hong,Liu, Yizhou,Meng, Dongfang,Scott, Jeremy,Shevlin, Michael,Tu, Qiang,Xu, Feng
, (2020)
Relebactam, a potent β-lactamase inhibitor, in combination with Primaxin is an FDA-approved (Recarbrio) treatment for serious and antibiotic-resistant bacterial infections. An efficient synthesis of key chiral piperidine intermediate 1 suitable for large-scale preparation of relebactam is described. The key steps include a unique highly diastereoselective FeCl3·6H2O/NaBH4 reduction of a chiral oxime ether and chemoselective amidation of the resulting unprotected pipecolic acid. Nuclear magnetic resonance studies and density functional theory calculations were carried out on the substrate-Fe(III) complexes, which shed light on diastereoselective reduction.
Synthesis of bicyclic β-lactamase inhibitor relabactam derivatives from a relabactam intermediate
Yang, Shu-Wei,Linghu, Xin,Smith, Elizabeth,Pan, Jianping,Sprague, Victoria,Su, Jing
supporting information, p. 2838 - 2841 (2017/06/27)
We have developed highly efficient chemistry to prepare two key intermediates from a Relabactam intermediate available from the process chemistry. The new intermediates enabled us to quickly synthesize other Ralebactam derivatives such as compound 1.
CRYSTALLINE FORMS OF DIAZABICYCLOOCTANE DERIVATIVE AND PRODUCTION PROCESS THEREOF
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Paragraph 0205; 0206, (2016/10/11)
A crystalline form of a diazabicyclooctane derivative represented by the following Formula (VII), and processes for producing the same:
