Chao Li

US Patent:

20200024290, Jan 23, 2020

Filed:

Mar 14, 2018

Appl. No.:

16/495907

Inventors:

- La Jolla CA, US
Chao Li - San Diego CA, US
Jie Wang - San Diego CA, US
Arnab Kumar Chatterjee - San Diego CA, US
Manoj Kumar - San Diego CA, US
Shan Yu - San Diego CA, US
Kristen Ann Johnson - Santee CA, US
Tian Qin - Dallas TX, US
Ming Shang - San Diego CA, US

International Classification:

C07F 5/02
C07B 47/00
B01J 31/02
C07K 7/64

Abstract:

The invention is directed to methods of converting a carboxylic acid group in a compound, via a redox active ester, to a corresponding boronic ester by treatment with bis(pinacolato)diboron-alkyllithium complex in the presence of a ligand, a Ni(11) salt or a copper salt, and an Mg(11) salt, in the presence of an alkyllithium or a lithium hydroxide or alkoxide salt. The product pinacolato boronate ester can be cleaved to provide a boronic acid. The invention is also directed to methods of preparing various compounds of medical value comprising boronic acid groups, and to novel boronic-acid containing compounds of medicinal value, including an atorvastatin boronic acid analog, a vancomycin aglycone boronic acid analog, and boronic acid containing elastase inhibitors mCBK319, mCBK320, mCBK323, and RPX-7009.