Infrared spectrum of a single resin bead for real-time monitoring of solid-phase reactions

Yan, Bing; Kumaravel, Gnanasambandam; Anjaria, H. V.; Wu, Aiyin; Petter, Russell C.; Jewell, Charles; Wareing, James R.

doi:10.1021/jo00122a077

Cited by 142 publications

(94 citation statements)

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“…Occasionally, compounds were prepared on a larger scale and were characterized by NMR, after cleavage from the resin. The capability for high resolution structural elucidations of compounds, while covalently attached to the solid support, was reported in the literature [4,5] but not available to us in time for this study.…”

Section: Validation Of Reaction Sequencesmentioning

confidence: 99%

Combinatorial Libraries on Rigid Scaffolds: Solid Phase Synthesis of Variably Substituted Pyrazoles and Isoxazoles

Marzinzik

Felder

1997

Molecules

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Abstract:The synthesis of combinatorial compound libraries has become a powerful lead finding tool in modern drug discovery. The ability to synthesize rapidly, in high yield, new chemical entities with low molecular weight on a solid support has a recognized strategic relevance ("small molecule libraries"). We designed and validated a novel solid phase synthesis scheme, suitable to generate diversity on small heterocycles of the pyrazole and isoxazole type. Appropriate conditions were worked out for each reaction, and a variety of more or less reactive agents (building blocks) was utilized for discrete conversions, in order to exploit the system's breadth of applicability. Four sequential reaction steps were validated, including the loading of the support with an acetyl bearing moiety, a Claisen condensation, an α-alkylation and a cyclization of a β-diketone with monosubstituted hydrazines. In a second stage, the reaction sequence was applied in a split and mix approach, in order to prepare a combinatorial library built-up from 4 acetyl carboxylic acids (R 1 ), 35 carboxylic esters (R 2 ) and 41 hydrazines (R 4 ) (and 1 hydroxylamine) to yield a total of 11,760 compounds divided into 41 pyrazole sublibraries with 140 pairs of regioisomers and 1 isoxazole sublibrary of equal size.

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Section: Validation Of Reaction Sequencesmentioning

confidence: 99%

Combinatorial Libraries on Rigid Scaffolds: Solid Phase Synthesis of Variably Substituted Pyrazoles and Isoxazoles

Marzinzik

Felder

1997

Molecules

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“…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 Spectroscopy (FT-IR) including Raman FT-IR, 8,9 Attenuated Total Reflection 10 and FT-IR microspectroscopy 11 and KBr pellets by Infrared difference spectra. 12 Though invaluable, these techniques require instrumentation that is often prohibitively expensive.…”

Section: Introductionmentioning

confidence: 99%

An efficient monitoring technique for solid-phase reactions by KBr pellets/FT-IR using methyl p-aminobenzoate synthesis assisted by microwave radiation on merrifield resin

Antonow¹,

Graebin²,

Eifler‐Lima³

2004

J. Braz. Chem. Soc.

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O uso de pastilhas de KBr em espectroscopia de infravermelho foi investigado para a monitorização de reações em fase sólida. A síntese do p-aminobenzoato de metila na Resina Merrifield (RM) é descrita como um modelo para esta técnica, a qual permite que o progresso das três etapas da síntese sejam monitoradas.The use of KBr pellets in infrared spectroscopy has been investigated for monitoring solidphase 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.

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“…Although such methodology presents several synthetic advantages such as reactions driven to completion by the use of excess reagents, important analytical limitations are imparted by the fact that standard spectroscopic analyses which imply sample dissolution in appropriate solvents cannot be performed. Cross-polarization magic angle spinning (CPMAS) NMR 2 and IR 3,4 have been used to follow polymer-supported syntheses. The former technique has been mainly applied to the control of solid-phase peptide syntheses for anchored chains bearing at most eight residues.…”

Section: Introductionmentioning

confidence: 99%

Imaging time-of-flight secondary ion mass spectrometry of solid-phase peptide syntheses

et al. 1999

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Infrared spectrum of a single resin bead for real-time monitoring of solid-phase reactions

Cited by 142 publications

References 0 publications

Combinatorial Libraries on Rigid Scaffolds: Solid Phase Synthesis of Variably Substituted Pyrazoles and Isoxazoles

Combinatorial Libraries on Rigid Scaffolds: Solid Phase Synthesis of Variably Substituted Pyrazoles and Isoxazoles

An efficient monitoring technique for solid-phase reactions by KBr pellets/FT-IR using methyl p-aminobenzoate synthesis assisted by microwave radiation on merrifield resin

Imaging time-of-flight secondary ion mass spectrometry of solid-phase peptide syntheses

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