Monitoring of Solid-Phase Reactions

OLIGOSACCHARIDE SYNTHESIS ON SOLID, SOLUBLE POLYMER. AND TAG SUPPORTS 

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In situ IR spectral monitoring of solid-phase reactions carried out in dichloro-methane, using a flow-through cell [170, 171] has also been described. 

Chan, T. Y. Chen, R. Sofia, M. J. Smith, B. C. Glennon, D. High Throughput On-Bead Monitoring of Solid Phase Reactions by Diffuse Reflectance Infrared Fourier Transform Spectroscopy (DRIFTS), Tetrahedron Lett. 1997, 38, 2821. 

Yan B, Kumaravel HA, Wu A, Petter RC, Jewell C, Wareing J, Infrared spectrum of a single resin bead for real time monitoring of solid phase reactions, J. Org. Chem., 60 5736-5738, 1995. 

TY Chan, R Chen, MJ Sofia, BC Smith, D Glennon. High throughput on-bead monitoring of solid phase reactions by diffuse reflectance infrared Fourier transform spectroscopy (DRIFTS). Tetrahedron Lett 38 2821-2824, 1997. 

Micro-IR spectra were used for real-time monitoring of solid phase reactions (12,15,16) and, utilizing deuterium isotope containing protecting groups, for quantitative infrared analysis of solid phase, resin-bound chemical reactions (13). 

The first use of this method for the monitoring of solid-phase reactions was described by Yan et al. [20]. Polystyrene hydroxymethyl resin as starting material was reacted with adipinic acid chloride and dipropargyle amine (Fig. 16.7). 

IR-microscopy allows the monitoring of solid-phase reactions during the time course analogous to FT-ATR-IR methods described above. Therefore, resin beads are removed from the reaction mixture at certain time intervals, washed and analyzed. The relation of... 

The use of deuterated reactants permits the real-time monitoring of solid-phase reactions via IR-microscopy. A few resin beads were trapped in a flow-through cell which can be charged with solvents and reagents using an HPLC pump. These beads were analyzed during the amidation of amino methyl polystyrene resin with deuterated benzoic acid, demonstrating that the reaction was complete after 12.7 min [36,37]. 

Yanl995 Yan, B., Kumaravel, G., Anjaria, H., Wu, A., Petter, R.C., Jewell, C.F., Jr. and Wareing, J.R., Infrared Spectrum of a Single Resin Bead for Real-Time Monitoring of Solid-Phase Reactions, J. Org. Chem., 60 (1995) 5736-5738. 

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