One-pot acylation and fractional crystallization: preparation of optically active serinol monobenzoates |
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| Institution: | 1. College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China;2. First Teaching Hospital of Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China;3. School of Science, Hebei University of Science&Technology, Shijiazhuang 050018, China;1. Organic Chemistry Department of Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russian Federation;2. Analytical Chemistry Department of Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russian Federation;3. Interdisciplinary Center for Analytical Microscopy of Kazan Federal University, Kremlevskaya, 18, 420008 Kazan, Russian Federation;1. Universitat Rovira i Virgili, Tarragona, 43007, Spain;2. Universidad de Costa Rica, San José, 2060, Costa Rica;3. Institute for Integrated Catalysis, Pacific Northwest National Laboratory, P.O. Box 999, MS K8-86, Richland, WA 99352, USA;4. Departamento de Engenharia Química, Universidade Federal de São Carlos, São Carlos, Brazil;5. Institut de Tècniques Energètiques, Universitat Politècnica de Catalunya, Spain;6. Universidad de Concepción, Facultad de Ciencias Químicas, Casilla 160C, Concepción, Chile;1. Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, SE-106 91 Stockholm, Sweden;2. The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States;3. Center for Supramolecular Chemistry and Catalysis, Shanghai University, Shanghai 200444, China |
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| Abstract: | Mono-O-acylation of (R)-2-(α-methylbenzyl)amino-1,3-propanediol 1 with 4-nitrobenzoyl chloride and DMAP in dichloromethane at room temperature gave crystals of optically active (2S,αR)-3-hydroxy-2-(α-methylbenzyl)aminopropyl 4-nitrobenzoate hydrochloride (2S)-2a·HCl] in 33% yield by fractional crystallization. Optically active oxazolidinones, aziridines, and serinol derivatives were synthesized from the benzoate (2S)-2a. |
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