A practical synthesis of 3-ethyl-l-norvaline |
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| Institution: | 1. Wyeth Research, Chemical and Screening Sciences, PO Box CN 8000, Princeton, NJ 08543, USA;2. Wyeth Research, Chemical and Screening Sciences, 401 N. Middletown Road, Pearl River, NY 10965, USA;3. Institute on Membrane Technology, National Research Council of Italy, ITM-CNR, Via P. Bucci Cubo 17C, 87036 Rende (CS), Italy;4. Molecular Imaging and Photonics, Faculty of Bioengineering Sciences, KU Leuven, Celestijnenlaan 200d - box 2425, 3001 Leuven, Belgium;5. Laboratoire de Génie Chimique, Université de Toulouse, CNRS, INPT, UPS, Toulouse, France;1. School of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan 410083, PR China;2. State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin 300071, PR China;1. Insight: Centre for Data Analytics, National Centre for Sensor Research, Dublin City University, Dublin, Ireland;2. Mondragon Unibertsitatea, Arrasate-Mondragón, Spain;3. Ikerbasque, Basque Foundation for Science, Bilbao, Spain;4. Microfluidics UPV/EHU Cluster, Analytical Chemistry Department, University of the Basque Country UPV/EHU, Vitoria-Gasteiz, Spain |
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| Abstract: | An efficient process for the synthesis of 3-ethyl-l-norvaline has been developed. The route makes use of a Strecker reaction, whereby (S)-(?)-α-methylbenzylamine acts as a chiral auxiliary to provide nearly diastereomerically pure α-amino nitrile. Crystallization-induced asymmetric transformation enhances the yield and diastereomeric ratio and allows for efficient isolation of the product. The amino nitrile intermediate is converted to enantiomerically pure 3-ethyl-l-norvaline in three steps. |
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