One-pot conversion of carboxylic acids to amides by in situ generated N-hydroxysuccinimide esters

ORGN 479

Misoo Kim, mkim@hnu.hankyong.ac.kr, Department of Basic Science, Hankyong National University, # 67 Seogjung-Dong, 456-749 Ansung, Kyonggi-Do, South Korea and Ki-Jong Han, jisuhan@unitel.co.kr, Department of Molecular Science and Technology, Ajou University, 443-749 Suwon, Kyonggi-Do, South Korea.
The formation of the amide bond is one of the fundamental reactions in organic synthesis. Most of the preparative methods for amides are based on the reaction of an activated carboxylic acid with an amine. N-Hydroxysuccinimide esters of carboxylic acids are usually prepared by reaction of the carboxylic acids with N-hydroxysuccinimide using dicyclohexylcarbodiimide (DCC). When DCC is used in coupling reactions, an equimolar amount of urea (DCU) is formed and cause difficulties in purification of the main product. We have developed an efficient one-pot procedure for the preparation of amides from carboxylic acids under simple conditions. N-Hydroxysuccinimide esters of carboxylic acids, formed in situ from carboxylic acids and N-hydroxysuccinimide in the presence of triphosgene, react with amines to give amides in high yields. The results of this transformation will be presented.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006