Solid-phase synthesis of a library of hydroxyproline derivatives
| Autor: | Mark R. Player, and Richard S. Pottorf, Anne L. Vergnon |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
Aldehydes
Magnetic Resonance Spectroscopy Tertiary amine Alkylation Chemistry Acylation Benzenesulfonates Alcohol General Chemistry Reductive amination chemistry.chemical_compound Hydroxyproline Solid-phase synthesis Alcohols Trifluoroacetic acid Organic chemistry Trifluoroacetic Acid Mitsunobu reaction Indicators and Reagents Phenols |
| Zdroj: | Journal of combinatorial chemistry. 6(1) |
| ISSN: | 1520-4766 |
| Popis: | The synthesis of a library of N-alkylated O-arylated hydroxyproline derivatives has been achieved on solid phase. The choice of O-protection and the optimization of the Mitsunobu reaction involving a secondary alcohol were key to the success of this synthesis. First, acylation of resin-bound amines with N-Fmoc-O-THP-hydroxyproline was accomplished readily. Subsequent deprotection of the Fmoc and reductive amination with different aldehydes resulted in the tertiary amine intermediate. The deprotection of the THP group by p-toluenesulfonic acid was followed by a Mitsunobu reaction with a series of phenols. Finally, the products were cleaved from the resin using trifluoroacetic acid to produce a 10 200 member library. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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