Phase Separation Macrocyclization in a Complex Pharmaceutical Setting: Application toward the Synthesis of Vaniprevir
| Autor: | Michaël Raymond, Anne-Catherine Bédard, Shawn K. Collins, Éric Godin |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Cyclopropanes
Sulfonamides Indoles Molecular Structure Proline 010405 organic chemistry Continuous flow Stereochemistry Macromolecular Substances Vaniprevir Lactams Macrocyclic Organic Chemistry Isoindoles 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Dilution chemistry.chemical_compound chemistry Cyclization Leucine Alkynes PEG ratio Microwaves |
| Zdroj: | The Journal of organic chemistry. 82(14) |
| ISSN: | 1520-6904 |
| Popis: | A phase separation/continuous flow strategy employing an oxidative Glaser–Hay coupling of alkynes has been applied toward the synthesis of the macrocyclic core of complex pharmaceutical vaniprevir. The phase separation/continuous flow strategy afforded similar yields at 100–500 times the concentration and at shorter reaction times than common slow addition/high dilution techniques. In addition, dendritic PEG cosolvents were employed in the phase separation strategy for the first time and shown to allow productive macrocyclization at concentrations up to 200 mM. |
| Databáze: | OpenAIRE |
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