Efficient one-pot procedure for the synthesis of N-hydroxysuccinimide esters of carboxylic acids using N-hydroxysuccinimide and triphosgene

ORGN 123

Misoo Kim, mkim@hnu.hankyong.ac.kr, Department of Basic Science, Hankyong National University, # 67 Seogjung-Dong, 456-749 Ansung, Kyonggi-Do, South Korea, Hagyoung Lee, hlee@mail.wsu.edu, Department of Chemical Engineering, 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.
N-Hydroxysuccimide esters of carboxylic acids have been widely used in organic synthesis as reactive acylating reagents. These active esters are especially useful as intermediates in the synthesis of peptides and proteins since they acylate primary amines to give the amides in high yields. We have developed a new and convenient one-pot procedure for the preparation of N-hydroxysuccinimide esters of carboxylic acids using N-hydroxysuccinimide and triphosgene as an acid activator. A variety of carboxylic acids can be easily and rapidly converted to the corresponding N-hydroxysuccinimido esters at room temperature. The results of this transformation will be presented.