Demonstration on Pilot-Plant Scale of the Utility of 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) as a Catalyst in the Efficient Amidation of an Unactivated Methyl Ester
- 30 November 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Process Research & Development
- Vol. 16 (12), 1967-1969
- https://doi.org/10.1021/op300210j
Abstract
The utility of 1,5,7-triazabicyclo[4.4.0]dec-5-ene as a reagent to facilitate efficient amide formation by reaction of an amine with an unactivated ester was demonstrated on pilot-plant scale as a key step in the synthesis of an H-PGDS inhibitor.Keywords
This publication has 8 references indexed in Scilit:
- Metal-catalysed approaches to amide bond formationChemical Society Reviews, 2011
- Evolution of amide bond formationArkivoc, 2010
- Cyclic Guanidine Organic Catalysts: What Is Magic About Triazabicyclodecene?The Journal of Organic Chemistry, 2009
- Mild and Efficient DBU-Catalyzed Amidation of CyanoacetatesOrganic Letters, 2009
- Amide bond formation: beyond the myth of coupling reagentsChemical Society Reviews, 2008
- A convenient aminolysis of esters catalyzed by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) under solvent-free conditionsTetrahedron Letters, 2007
- Triazabicyclodecene: A Simple Bifunctional Organocatalyst for Acyl Transfer and Ring-Opening Polymerization of Cyclic EstersJournal of the American Chemical Society, 2006
- Amide bond formation and peptide couplingTetrahedron, 2005