2020
DOI: 10.1021/acs.oprd.0c00281
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A General Kilogram Scale Protocol for Suzuki–Miyaura Cross-Coupling in Water with TPGS-750-M Surfactant

Abstract: The development of a kilogram scale protocol for a Suzuki−Miyaura cross-coupling step toward the synthesis of the drug candidate LSZ102 is described. Particularly, the use of the surfactant TPGS-750-M in water as a medium for the transformation and its impact on the selectivity and quality are reported. Minimization of typical impurities generated during the cross-coupling (e.g., dehalogenation) has been in focus during our study. The environmental and cost impacts using such a process are also discussed.

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Cited by 55 publications
(49 citation statements)
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“…As an example for option 1 (no pretreatment), we like to discuss the liquid waste streams from the recently described C−C coupling in the synthesis of the active pharmaceutical ingredient (API) 1 shown in Scheme 2. 39 In this case, the extractive work-up with MeTHF involves distillation of acetone, separation of the aqueous phase, and washing of the organic layer with aqueous solutions. Crystallization of the product and filtration leaves an organic mother liquor.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…As an example for option 1 (no pretreatment), we like to discuss the liquid waste streams from the recently described C−C coupling in the synthesis of the active pharmaceutical ingredient (API) 1 shown in Scheme 2. 39 In this case, the extractive work-up with MeTHF involves distillation of acetone, separation of the aqueous phase, and washing of the organic layer with aqueous solutions. Crystallization of the product and filtration leaves an organic mother liquor.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Forschung im Bereich der nachhaltigen Chemie ist stark anwendungsorientiert und findet nicht aus dem akademischen Elfenbeinturm heraus statt. Dass Industriekooperationen zur Mizellenkatalyse erfolgreich sein können, zeigt die Anwendung im Kilogrammmaßstab, etwa in den Unternehmen Novartis (Abbildung oben), 13) Evonik 14) und Takeda. 15) Ungeachtet dieser Erfolgsgeschichte der Mizellenkatalyse sind noch Herausforderungen zu überwinden, etwa im Hinblick auf die Anwendung in kontinuierlichen Verfahren.…”
Section: Anwendungsorientiertunclassified
“…Very often, as the complexity of the product increases, its solubility decreases which readily induces its precipitation from such media [46]. When the product is still partitioning in the various phases, a streamlined extractive work-up with a desirable and sustainable organic solvent enables isolation and purification in a practical manner, besides ensuring complete depletion of potential residual surfactant [47] (see Scheme 3).…”
Section: Water Chemistry Enabled By Surfactantsmentioning
confidence: 99%