pH-Dependent Degradation of T3P-Related Byproducts

Propylphosphonic anhydride, or T3P, is a commonly used reagent for amidation reactions with numerous examples of application on scale. One process-friendly aspect of the reagent is the ease of workup, in which quench and extraction or crystallization from aqueous systems should remove any residual T...

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Bibliographic Details
Published in:Organic process research & development 2021-03, Vol.25 (3), p.621-626
Main Authors: Davidson, Andrew, Foley, David A, Frericks-Schmidt, Heather, Ruggeri, Sally Gut, Herman, Madeline, LaCasse, Shawn, Liu, Yizhou, McInturff, Emma L, Morris, Ronald, Mugheirbi, Naila, Samas, Brian, Sarkar, Aritra, Singer, Robert A, Witkos, Faith, Yu, Shu
Format: Article
Language:English
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Summary:Propylphosphonic anhydride, or T3P, is a commonly used reagent for amidation reactions with numerous examples of application on scale. One process-friendly aspect of the reagent is the ease of workup, in which quench and extraction or crystallization from aqueous systems should remove any residual T3P or related byproducts. This communication discusses the isolation and characterization of a T3P degradation byproduct and removal of the water-soluble byproduct by washing or further degradation at low pH. A second example demonstrates the degradation of a T3P-related phosphonic ester at low pH.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.0c00431