Solution-Phase Synthesis of Mixed Amide Libraries by Simultaneous Addition of Functionalities (SPSAF) to a Diketopiperazine Tetracarboxylic Acid Scaffold Monitored by GC Analysis of Isobutyl Alcohol
✍ Scribed by Massimo Falorni; Giampaolo Giacomelli; Andrea Porcheddu; Maurizio Taddei
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 357 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
A symmetric diketopiperazine scaffold 2 has been prepared in a very simple two-step procedure from l-aspartic acid dimethyl ester. This product (a tetracarboxylic acid equally protected at the two symmetric positions) has been employed as a template for the synthesis of mixed amide libraries in the solution phase using the SPSAF (simultaneous addition of functionalities) strategy. By judicious choice of the amines employed, it is possible to prepare parallel libraries containing hundreds of products using just a small number of different amines. We have also developed a simple method for monitoring the required conversion of the acid into amides based on an assay of the amount of iBuOH (deter-