ORGN 625 |
| Shahnaz Ghassemi, Biotage, 1725 Discovery Drive, Charlottesville, VA 22911 |
| The tert-Butoxycarbonyl group (abbreviated Boc or t-Boc) remains one of the most frequently used amino protecting groups in organic synthesis. Its inertness towards catalytic hydrogenolysis and extreme resistance towards basic and nucleophilic reagents makes it an ideal orthogonal partner to benzyl esters and carbamates. Boc cleavages are carried out under strong acidic conditions utilizing trifluoroacetic acid (CF3COOH) (TFA) either neat or with solvent, typically CH2Cl2. Since TFA is a volatile, harsh, corrosive reagent a search for alternative method of de-blocking has been ongoing. In an alternate Boc-cleavage methodology, de-protection of a BOC-amine in a batch process was carried out using a strong acidic ion-exchange resin over 12-24 hours. This work illustrates a new technique combining microwave irradiation with silica-supported sulfonic acid media to facilitate the simultaneous de-protection and flash purification of BOC-amines using a catch and release strategy. A small library of primary and secondary amines was prepared and a summary of this small library synthesis will be presented. |
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |