Process for the preparation of 2-(S)-piperazinecarboxylic acid by continuous resolution via diastereomeric salt pairs

✍ Scribed by Klaus Stingl; Matthias Kottenhahn; Karlheinz Drauz

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 195 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00053-0

✦ Synopsis

Continuous resolution of 2-piperazinecarboxylic acid 2 with (S)-camphor-10-sulfonic acid as resolving and epimerisation agent affords 2-(S)-piperazinecarboxylic acid (S)-dicamphor-10-sulfonate 3 in 62% isolated yield and >99% ee. (~) 1997 Elsevier Science Ltd Optically active amino acids and derivatives have generated widespread interest in various areas, especially in the agrochemicals (as herbicides, insecticides, fungicides), food (as peptide sweeteners), and pharmaceutical industries (as infusion solutions or therapeutic agents). During the last decade, nonproteinogenic amino acids, and derivatives thereof, have received particular attention in the synthesis of biologically active compounds. One example is 2-(S)-piperazinecarboxylic acid 1, because its Nten-butyl amide is an important intermediate in the preparation of Merck HIV protease inhibitor indinavir (Crixivan®) 1 (Scheme 1).