Insights into Fast Amide Couplings in Aqueous Nanomicelles,Organic Process Research & Development

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Insights into Fast Amide Couplings in Aqueous Nanomicelles
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2021-07-08 , DOI: 10.1021/acs.oprd.1c00203
Sudripet Sharma ₁ , Gaganpreet Kaur ₁ , Sachin Handa ₁

Affiliation

1-Ethyl-3-(3-(dimethylamino)propyl)-carbodiimide (EDC•HCl) has both lipophilic and hydrophilic regions, causing self-aggregation (also called nanoparticle formation) in an aqueous medium containing PS-750-M amphiphile. Kinetic and proton nuclear magnetic resonance studies were used to probe the effect of different organic bases on the potential nanoparticle formation of EDC•HCl. It also reveals why the pyridine base works better under micellar conditions. The methodology was examined on the multigram scale synthesis of bioactive molecules, where excellent reaction yields were obtained without product epimerization while maintaining a shorter reaction time.

中文翻译：

对水性纳米胶束中快速酰胺偶联的深入了解

1-Ethyl-3-(3-(二甲氨基)丙基)-碳二亚胺 (EDC•HCl) 具有亲脂性和亲水性区域，在含有 PS-750-M 两亲物的水性介质中引起自聚集（也称为纳米颗粒形成）。动力学和质子核磁共振研究用于探测不同有机碱对 EDC•HCl 潜在纳米颗粒形成的影响。它还揭示了为什么吡啶碱在胶束条件下效果更好。该方法在生物活性分子的多克规模合成上进行了检查，其中在没有产物差向异构化的情况下获得了优异的反应收率，同时保持了更短的反应时间。

更新日期：2021-08-20

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