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Fast Amide Couplings in Water: Extraction, Column Chromatography, and Crystallization Not Required

Sudripet Sharma, Nicklas W. Buchbinder, Wilfried M. Braje and Sachin Handa*

*Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States, Email: sachin.handalouisville.edu

S. Sharma, N. W. Buchbinder, W. M. Braje, S. Handa, Org. Lett., 2020, 22, 5737-5740.

DOI: 10.1021/acs.orglett.0c01676 (free Supporting Information)


Abstract

The L-proline-based amphiphile PS-750-M enables extremely fast amide couplings in water mediated by 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (without hydroxybenzotriazole). Product precipitation and isolation by filtration completely avoids the use of organic solvent. This methodology avoids product epimerization and is scalable.

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Key Words

amides, green chemistry


ID: J54-Y2020