A convenient method for the preparations of carboxamides and peptides by using di(2-pyridyl) carbonate and O,O '-di(2-pyridyl) thiocarbonate as dehydrating reagents

Authors
Shiina, I Suenaga, Y Nakano, M Mukaiyama, T
Citation
I. Shiina et al., A convenient method for the preparations of carboxamides and peptides by using di(2-pyridyl) carbonate and O,O '-di(2-pyridyl) thiocarbonate as dehydrating reagents, B CHEM S J, 73(12), 2000, pp. 2811-2818
Citations number
35
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
ISSN journal
00092673 → ACNP
Volume
73
Issue
12
Year of publication
2000
Pages
2811 - 2818
Database
ISI
SICI code
0009-2673(200012)73:12<2811:ACMFTP>2.0.ZU;2-L
Abstract
Preparations of carboxamides and peptides are performed in high yields from free carboxylic acids and amines by dehydration condensation using di(2-py ridyl) carbonate (DPC) or O,O'-di(2-pyridyl) thiocarbonate (DPTC) in the pr esence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP). The forma tion of 2-pyridyl esters, key intermediates of the reaction, from carboxyli c acids by using DPC proceeded faster than by using DPTC; therefore, the fo rmer carbonate is more efficiently employed in the above condensation react ions.