Novel quenchers for solution phase parallel synthesis

Nikam, Sham S.; Kornberg, Brian E.; Ault-Justus, Stephanie E.; Rafferty, Michael

doi:10.1016/s0040-4039(97)10781-x

Cited by 25 publications

(16 citation statements)

References 7 publications

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“…[229,240,241] Scheme 46 shows an example of amine SERs 52 and 53 to remove excess isocyanate. [229,240,241] Scheme 46 shows an example of amine SERs 52 and 53 to remove excess isocyanate.…”

Section: Purification By Sequestration-enabling Reagent Techniquementioning

confidence: 99%

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Tzschucke

Märkert

Bannwarth

et al. 2002

Angew. Chem. Int. Ed.

339

133

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The shift of paradigm in combinatorial chemistry, from large compound libraries (of mixtures) on a small scale towards defined compound libraries where each compound is prepared in an individual well, has stimulated the search for alternative separation approaches. The key to a rapid and efficient synthesis is not only the parallel arrangement of reactions, but simple work-up procedures so as to circumvent time-consuming and laborious purification steps. During the initial development stages of combinatorial synthesis it was believed that rational synthesis of individual compounds could only be achieved by solid-phase strategies. However, there are a number of problems in solid-phase chemistry: most notably there is the need for a suitable linker unit, the limitation of the reaction conditions to certain solvents and reagents, and the heterogeneous reaction conditions. Further disadvantages are: the moderate loading capacities of the polymeric support and the limited stability of the solid support. In the last few years several new separation techniques have been developed. Depending on the chemical problem or the class of compounds to be prepared, one can choose from a whole array of different approaches. Most of these modern separation approaches rely on solution-phase chemistry, even though some of them use solid-phase resins as tools (for example, as scavengers). Several of these separation techniques are based on liquid-liquid phase separation, including ionic liquids, fluorous phases, and supercritical solvents. Besides being benign with respect to their environmental aspects, they also show a number of advantages with respect to the work-up procedures of organic reactions as well as simplicity in the isolation of products. Another set of separation strategies involves polymeric supports (for example, as scavengers or for cyclative cleavage), either as solid phases or as soluble polymeric supports. In contrast to solid-phase resins, soluble polymeric supports allow reactions to be performed under homogeneous conditions, which can be an important factor in catalysis. At the same time, a whole set of techniques has been developed for the separation of these soluble polymeric supports from small target molecules. Finally, miscellaneous separation techniques, such as phase-switchable tags for precipitation by chemical modification or magnetic beads, can accelerate the separation of compounds in a parallel format.

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“…[229,240,241] Scheme 46 shows an example of amine SERs 52 and 53 to remove excess isocyanate. [229,240,241] Scheme 46 shows an example of amine SERs 52 and 53 to remove excess isocyanate.…”

Section: Purification By Sequestration-enabling Reagent Techniquementioning

confidence: 99%

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Tzschucke

Märkert

Bannwarth

et al. 2002

Angew. Chem. Int. Ed.

339

133

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“…Auch nucleophile Abtrennungsreagentien wurden beschrieben 229, 240, 241. In Schema ist die Anwendung der Amin‐SERs 52 und 53 zum Entfernen von nichtumgesetztem Isocyanat dargestellt.…”

Section: Polymergestützte Trenn‐ Und Reinigungsverfahrenunclassified

Moderne Trennverfahren zur effizienten Aufarbeitung in der organischen Synthese

et al. 2002

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Die kombinatorische Synthese [1,2] wird als eine der Schl¸s-seldisziplinen f¸r den konstanten Nachschub an chemischen Verbindungen angesehen, die auf biologische Aktivit‰t gegen¸ber der immens wachsenden Zahl biologischer Zielmolek¸le getestet werden kˆnnen. Zusammen mit dem Hochdurchsatz-Screening und einem effizienten Datenmanagement wird ihre Anwendung den Prozess der Wirkstoffentdeckung zweifelsohne beschleunigen. Urspr¸nglich konzentrierte sich die Kombinatorische Chemie auf die schnelle Synthese von hochkomplexen Gemischen mit winzigen An-

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“…54 The choice of which linking reagent to use was dictated by the phaseswitching purification procedure employed (cationic or anionic solid phase extraction). Entries B and C illustrate the use of either glycine 55 or sarcosine 56 to react with aldehydes, isothiocyanates, acid chlorides, or sulfonyl chlorides to impart acidic functionality to derivatized species 57, 58, or 60. Phase-switching isolation of these derivatized reactants away from desired products was accomplished by solid-phase or liquid-phase extraction.…”

Section: A Use Of Bifunctional Linking Reagents To Match Functionalimentioning

confidence: 99%

Phase-trafficking reagents and phase-switching strategies for parallel synthesis

Flynn

1999

Med. Res. Rev.

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Novel quenchers for solution phase parallel synthesis

Cited by 25 publications

References 7 publications

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Modern Separation Techniques for the Efficient Workup in Organic Synthesis

Moderne Trennverfahren zur effizienten Aufarbeitung in der organischen Synthese

Phase-trafficking reagents and phase-switching strategies for parallel synthesis

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