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Large Scale Amide Coupling: Triazine-Based Coupling Reagents

591 阅读 2020-09-15 10:06:02 上传

以下文章来源于 计算语言学


The mechanism for acid activation with cyanuric chloride has generally been described as proceeding via acid chloride formation.

         

                 

However, there has also been a report from the process chemistry group at Rohm and HaasCompany in which an acid chloride from cyanuric chloride was not detected; instead, acid activation was proposed to take place via an activated ester.


The resulting cyanuric acid byproduct can be easily removed during workup via filtration or basic washes.

 

CDMT hasbeen shown to be effective at reducing epimerization and, also, to work with sterically hindered primary and secondary alkyl and aryl amines.

An advantage of DMTMM is that it can be employed for amide bond formation in alcoholic or aqueous solvents without the generation of the corresponding esters or hydrolysis product.


Suppressing Racemization during a DMTMM Actived Amide Formation

A General and Practical Alternative to Polar Aprotic Solvents




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