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Solid-phase library synthesis of alkoxyprolines.

A M Boldi¹, J M Dener, T P Hopkins

¹ChemRx Advanced Technologies, Inc., A Discovery Partners International Company, 385 Oyster Point Boulevard, Suite 1, South San Francisco, California 94080, USA.

Journal of Combinatorial Chemistry

|July 10, 2001

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This study introduces a novel method for synthesizing alkoxyprolines using a specialized solid support. The developed technique ensures high purity of the final alkoxyproline library, advancing chemical synthesis strategies.

Area of Science:

Organic Chemistry
Medicinal Chemistry
Synthetic Chemistry

Background:

Alkoxyprolines are valuable proline derivatives with diverse applications.
Efficient synthesis of alkoxyproline libraries is crucial for drug discovery and chemical biology.
Existing methods may lack efficiency or require harsh conditions.

Purpose of the Study:

To develop a robust and efficient solid-phase synthesis strategy for alkoxyprolines.
To create a diverse library of alkoxyproline derivatives.
To ensure high purity of the synthesized compounds.

Main Methods:

Utilized an acid-stable, nucleophile-cleavable solid support.
Employed a hydroxythiophenol linker derived from Merrifield resin.

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Performed esterification, BOC deprotection, acylation, and amine-mediated cleavage.

Purified products using supported liquid-liquid extraction.

Main Results:

Successfully synthesized a library of alkoxyprolines.
Achieved high purity of the final alkoxyproline products.
Demonstrated the utility of the solid support and cleavage strategy.

Conclusions:

The developed solid-phase synthesis is effective for generating alkoxyproline libraries.
The method offers a reliable route to pure alkoxyproline derivatives.
This approach facilitates the exploration of alkoxyproline chemical space.