Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization.,ACS Combinatorial Science

当前位置： X-MOL 学术 › ACS Comb. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Immobilized Carbodiimide Assisted Flow Combinatorial Protocol to Facilitate Amide Coupling and Lactamization.
ACS Combinatorial Science Pub Date : 2020-04-22 , DOI: 10.1021/acscombsci.0c00001
Christian Dankers ₁ , Joseph Tadros ₁ , David G Harman _{2,

3} , Janice R Aldrich-Wright _{1,

4} , Thanh V Nguyen ₅ , Christopher P Gordon _{1,

3}

Affiliation

Through a screen of over one hundred and 30 permutations of reaction temperatures, solvents, carbodiimide resins, and carbodiimide molar equivalences, in the presence, absence, or combination of diisopropylamine and benzotriazole additives, a convenient and first reported carbodiimide polymer-assisted flow approach to effect amide coupling and lactamization was developed. The protocol entails injecting a single solution (1:9 dimethylformamide: dichloromethane) containing a carboxylic acid and an amine or linear peptide sequence into a continuous stream of dichloromethane. The protocol remained viable in the absence of base, did not require carboxylate preactivation which, and in concert with minimal workup requirements, enabled the isolation of products in high yields. Compared to the utilization of untethered carbodiimide reagents, the flow procedure was also observed to provide a degree of racemization safety.

中文翻译：

固定化碳二亚胺辅助流动组合方案，以促进酰胺偶联和内酰胺化。

通过在存在，不存在二异丙胺和苯并三唑添加剂的情况下或将其组合使用时，对反应温度，溶剂，碳二亚胺树脂和碳二亚胺摩尔当量的一百三十多种排列进行筛选，一种便捷且首次报道的碳二亚胺聚合物辅助流动方法开发了酰胺偶联和内酰胺化作用。该方案需要将包含羧酸和胺或线性肽序列的单一溶液（1：9二甲基甲酰胺：二氯甲烷）注入连续的二氯甲烷流中。该方案在没有碱的情况下仍然可行，不需要羧酸盐预活化，这与最低限度的后处理要求相结合，能够以高收率分离出产物。与使用非限制碳二亚胺试剂相比，

更新日期：2020-04-13

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11