Abstract
The use of KBr pellets in infrared spectroscopy has been investigated for monitoring solid-phase reactions. Synthesis of the methyl p-aminobenzoate on Merrifield resin (MR) is described as a model for this technique, which allows the progress of its three on-bead reaction steps to be monitored throughout their duration.
Highlights
Solid Phase Organic Synthesis (SPOS)[1] involves the synthesis of molecules on chemically-inert insoluble polymers
Since the polymeric structure of the solid support remains unaltered during the entire reaction, it can be used as an internal reference, allowing the comparison of the additional and subtracted peaks
Any peak can be selected for this purpose, as long as it remains constant during the reaction
Summary
Solid Phase Organic Synthesis (SPOS)[1] involves the synthesis of molecules on chemically-inert insoluble polymers. High yields are often obtained because each reaction step can be driven virtually to completion by use of excess reagents. The ability to monitor solid-supported reactions is highly desirable when an ever-increasing diversity of chemical processes are becoming amenable to SPOS and, the production of combinatorial libraries for the rapid discovery of novel drug candidates. Even though the two classical approaches to control reactions, consisting of chromatography and NMR methodologies, work well in solution phase, some difficulties have been found to extending these methods to monitoring on-bead reactions. The main consequence is that solid-phase reactions are often left to run for longer than necessary (to ensure a complete reaction). Some methods have been employed in SPOS such as NMR gelphase spectroscopy or magic angle NMR spectroscopy,[2,3,4,5,6] fluorescence spectroscopy,[7] and Fourier Transform Infrared
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