1241589-35-4

Upstream product

• 1213399-90-6 (S)-2-(3-bromo-4-hydroxyphenyl)-2-((tert-butoxycarbonyl)amino)acetic acid 
• 189816-05-5 4-chloro-7-methoxy-2-phenylquinoline 
• 1428537-42-1 4-fluoro-7-methoxy-2-phenylquinoline 
• 20430-72-2 7-methoxy-2-phenylquinolin-4-ol 

Relevant academic research and scientific papers

One-pot, two-step, microwave-assisted palladium-catalyzed conversion of aryl alcohols to aryl fluorides via aryl nonaflates

A convenient procedure for converting aryl alcohols to aryl fluorides via aryl nonafluorobutylsulfonates (ArONf) is presented. Moderate to good one-pot, two-step yields were achieved by this nonaflation and microwave-assisted, palladium-catalyzed fluorination sequence. The reductive elimination step was investigated by DFT calculations to compare fluorination with chlorination, proving a larger thermodynamic driving force for the aryl fluoride product. Finally, a key aryl fluoride intermediate for the synthesis of a potent HCV NS3 protease inhibitor was smoothly prepared with the novel protocol.

Improved P2 phenylglycine-based hepatitis C virus NS3 protease inhibitors with alkenylic prime-side substituents

Phenylglycine has proved to be a useful P2 residue in HCV NS3 protease inhibitors. A novel π-π-interaction between the phenylglycine and the catalytic H57 residue of the protease is postulated. We hypothesized that the introduction of a vinyl on the phenylglycine might strengthen this π-π-interaction. Thus, herein is presented the synthesis and inhibitory potency of a series of acyclic vinylated phenylglycine-based HCV NS3 protease inhibitors. Surprisingly, inhibitors based on both d- and l-phenylglycine were found to be effective inhibitors, with a slight preference for the d-epimers. Furthermore, prime-side alkenylic extension of the C-terminal acylsulfonamide group gave significantly improved inhibitors with potencies in the nanomolar range (～35 nM), potencies which were retained on mutant variants of the protease.