2-Chlorotrityl Chloride and 4-Methylbenzhydryl Bromide Resin Loading Using the Mixture of Organic Solvents: A “Greener” Alternative to Dichloromethane and N,N-Dimethylformamide,Organic Process Research & Development

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2-Chlorotrityl Chloride and 4-Methylbenzhydryl Bromide Resin Loading Using the Mixture of Organic Solvents: A “Greener” Alternative to Dichloromethane and N,N-Dimethylformamide
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2021-12-27 , DOI: 10.1021/acs.oprd.1c00356
Maria Leko ₁ , Polina Filippova ₁ , Marina Dorosh ₁ , Karin Rustler ₂ , Thomas Bruckdorfer ₂ , Sergey Burov ₁

Affiliation

Common protocols for the loading of 2-CTC and MBH-Br resins presume the application of DCM, THF, or DMF; these solvents are considered as undesirable in accordance with modern regulatory rules. An alternative option implies the usage of rather expensive 2-MeTHF. Herein, we describe the application of an EtOAc/AcN (1:1) mixture as an efficient solvent alternative for the incorporation of the first amino acid. We show that the suggested reaction conditions ensure a loading level comparable to the usage of DCM, THF, 2-MeTHF, and DMF. The described procedure was designed for the kilogram-scale synthesis of a palmitoyl-hexapeptide.

中文翻译：

使用有机溶剂混合物装载 2-氯三苯甲基氯和 4-甲基二苯甲基溴树脂：二氯甲烷和 N,N-二甲基甲酰胺的“更环保”替代品

加载 2-CTC 和 MBH-Br 树脂的常用方案假定应用 DCM、THF 或 DMF；根据现代监管规则，这些溶剂被认为是不可取的。另一种选择意味着使用相当昂贵的 2-MeTHF。在这里，我们描述了 EtOAc/AcN (1:1) 混合物作为掺入第一个氨基酸的有效溶剂替代品的应用。我们表明，建议的反应条件确保负载水平与 DCM、THF、2-MeTHF 和 DMF 的使用相当。所描述的程序设计用于棕榈酰六肽的公斤级合成。

更新日期：2022-01-21

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