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Solid-phase library synthesis of alkoxyprolines.

The library synthesis of alkoxyprolines was achieved using an acid-stable, nucleophile-cleavable solid support. A hydroxythiophenol linker derived from Merrifield resin was esterified with the corresponding ethers of BOC-hydroxyproline. Removal of the BOC protecting group with trifluoroacetic acid followed by acylation gave solid-supported hydroxyproline derivatives. Cleavage from the solid support with excess primary amines or excess secondary amines followed by purification of the crude products from the excess amine by supported liquid-liquid extraction gave the alkoxyproline library in high purity.[1]

References

  1. Solid-phase library synthesis of alkoxyprolines. Boldi, A.M., Dener, J.M., Hopkins, T.P. Journal of combinatorial chemistry. (2001) [Pubmed]
 
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