Resin-Bound Coupling Reagent PS-Carbodiimide - C&EN Global

Eng. News , 2002, 80 (20), p 4. DOI: 10.1021/cen-v080n020.p004. Publication Date: May 20, 2002. Copyright © 2002 ... this:Chem. Eng. News 80, 20, XXX...
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Resin-Bound Coupling Reagent

PS-Carbodiimide PS-Carbodiimide is a tethered carbodiimide used for synthesis of amides, esters and activated esters. When used as a coupling reagent, the cyclohexylurea byproducts remain bound to the resin, greatly simplifying work up. The resin tether is designed to provide optimal reactivity combined with exceptional stability1. PS-Carbodiimide has been found to be more reactive and to give better results than other commercially available carbodiimides2*3. Amide Synthesis

If necessary, 1-hydroxybenzotriazole (HOBt) is added to the amide synthesis reaction to suppress a rearrangement to an unreactive acylurea. HOBt converts the reactive intermediate to the HOBt active ester, which then reacts with the amine to generate the amide. The HOBt is released and is readily scavenged with MP-Carbonate or PS-Trisamine. N=C=NΝ

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NHR 2