New Supports for Solid-Phase Organic Synthesis: Development of Cross- Linked Polytetrahydrofuran-Polystyrene Resins

Kim Janda,Thomas Hoeg-Jensen,Patrick Toy,Patrick Garibay

doi:10.3390/ecsoc-3-01755

Abstract

With the advent of combinatorial chemistry and automated synthesis there has been renewed interest in polymer-supported reactions.[1] However, it is evident from the literature that polymer supports used for other than peptide or nucleotide synthesis are, at present, far from optimized. It is not a trivial matter to identify new supports that are economically viable, exhibit satisfactory physical characteristics and that are inert to the diverse range of reagents/catalysts commonly involved in a multi-step combinatorial synthesis. Herein we describe a new class of resins that meet the criteria stated (vide supra). The resins are based on a set of polytetrahydrofuran (PTHF) cross-linkers and hold significant promise as polymer supports for solid-phase synthesis and combinatorial chemistry.

Highlights

Resins 2a-c were prepared by suspension polymerization of mixtures of 4-vinylbenzyl chloride (4-VBC), styrene and 1a-c, respectively. in 1, 2, 5 and 10 mole percent of the monofunctional monomers to afford 12 resins (Table 1)
Treatment of 6a-c with sec-BuLi and TMEDA was followed by trapping with p-anisaldehyde and cyclization to release phthalide 3 in greater than 95% purity, as determined by 1H NMR spectroscopy (Table 2)
The cleaved products were again determined to be greater than 95% pure as judged by 1H NMR spectroscopy

Summary

Introduction

Resins 2a-c were prepared by suspension polymerization of mixtures of 4-VBC, styrene and 1a-c, respectively. in 1, 2, 5 and 10 mole percent of the monofunctional monomers to afford 12 resins (Table 1). Resins 2a-c were prepared by suspension polymerization of mixtures of 4-VBC, styrene and 1a-c, respectively. The amount of swelling decreases as the level of crosslinking increases, even the 10% cross-linked resins swell significantly.

Results

Conclusion