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Performance Analysis and Model-Free Design of Deracemization via Temperature Cycles
Organic Process Research & Development ( IF 3.4 ) Pub Date : 2020-07-20 , DOI: 10.1021/acs.oprd.0c00266
Francesca Breveglieri 1 , Iaroslav Baglai 2 , Michel Leeman 3 , Willem L. Noorduin 2 , Richard M. Kellogg 3 , Marco Mazzotti 1
Affiliation  

Solid-state deracemization via temperature cycles is a technique that has been shown to be effective to isolate the pure enantiomer of a conglomerate-forming compound. This process has a large number of operating parameters that can be adjusted according to system-specific properties. On the one hand, this feature makes the process flexible and prone to optimization. On the other hand, the design space is so large that experimental optimization of the process can become long and cumbersome. In this work, we achieve two results. First, we show that deracemization via temperature cycles works very effectively for two new experimental systems, namely, the chiral compounds 2-(benzylideneamino)-2-(2-chlorophenyl)acetamide (CPG) and 3,3-dimethyl-2-((naphthalen-2-ylmethylene)amino)butanenitrile (tLEU). Second, we propose a new approach for the design of an effective deracemization process via temperature cycles for a new compound. Therefore, in this work, we investigate the effect of different operating conditions, namely, the initial enantiomeric excess, the cooling rate, the temperature range, and the catalyst concentration, on the performance of deracemization via temperature cycles for the new compounds CPG and tLEU and for N-(2-methylbenzylidene)phenylglycine amide (NMPA), which was already studied in a previous paper. On the basis of these outcomes, we conclude by proposing a model-free screening strategy for the design of an effective deracemization process via temperature cycles for a new compound.

中文翻译:

通过温度循环进行脱硝的性能分析和无模型设计

经由温度循环的固态脱硫是一种已显示出有效分离聚集物形成化合物的纯对映体的技术。该过程具有大量的操作参数,可以根据系统特定的属性进行调整。一方面,此功能使过程变得灵活且易于优化。另一方面,设计空间很大,以至于过程的实验优化可能会变得冗长而繁琐。在这项工作中,我们实现了两个结果。首先,我们证明了通过温度循环进行的脱硝作用对于两个新的实验系统非常有效,即手性化合物2-(亚苄基氨基)-2-(2-氯苯基)乙酰胺(CPG)和3,3-二甲基-2-( (萘-2-基亚甲基)氨基)丁腈(tLEU)。第二,我们提出了一种通过新化合物的温度循环设计有效脱硝工艺的新方法。因此,在这项工作中,我们通过温度循环研究了新化合物CPG和tLEU的不同操作条件(即初始对映体过量,冷却速率,温度范围和催化剂浓度)对脱硝性能的影响。和为N-(2-甲基亚苄基)苯基甘氨酸酰胺(NMPA),已在先前的论文中进行了研究。基于这些结果,我们最后提出了一种无模型的筛选策略,用于通过温度循环设计新化合物来设计有效的脱硝过程。
更新日期:2020-08-21
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