Facile syntheses of 4-(trifluoromethyl)-L-spinacine and 4-(trifluoromethyl)spinaceamine |
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| Affiliation: | 1. Institut für Pharmazeutische und Medizinische Chemie, Westfälische Wilhelms-Universität Münster, Corrensstraße 48, D-48149 Münster, Germany;2. Cells-in-Motion Cluster of Excellence (EXC 1003 – CiM), Westfälische Wilhelms-Universität Münster, Germany;1. Department of Fine Chemistry, Seoul National University of Science and Technology, Seoul, Republic of Korea;2. Department of Chemistry and Nano Science, Global Top 5 Research Program, Ewha Womans University, Seoul 120-750, Republic of Korea;1. Departament de Genètica, Universitat de Barcelona (UB); IBUB; CIBER de Enfermedades Raras (CIBERER), Av. Diagonal 645, E-08028, Barcelona, Spain;2. Research Unit on BioActive Molecules (RUBAM), Departament de Química Biomèdica, Institut de Química Avançada de Catalunya (IQAC-CSIC), Jordi Girona 18, 08034 Barcelona, Spain;3. Facultat de Farmàcia, Unitat de Química Farmacèutica (Unitat Associada al CSIC), Universitat de Barcelona (UB), Avda. Joan XXIII, s/n, 08028 Barcelona, Spain;4. Department of Cell and Molecular Biology, Uppsala University, Biomedical Center, Box 596, SE-751 24, Uppsala, Sweden;5. Departament de Química Biològica i Modeltzació Molecular, Institut de Química Avançada de Catalunya (IQAC-CSIC), Jordi Girona 18, 08034 Barcelona, Spain;6. Department of Enzymology and Cellular Function, Institute of Child Health, Athens 11527, Greece;7. Department of Medicinal Biochemistry, Academic Medical Center. Meibergdreef 15, 1105 AZ, Amsterdam, The Netherlands;1. Chair and Department of Medical Chemistry, Medical University, 4A Chodźki Street, 20-093 Lublin, Poland;2. Department of Biology and Genetics, Medical University, 4A Chodźki Street, 20-093 Lublin, Poland;3. Laboratory of Bioorganic Synthesis and Analysis, Chair and Department of Medical Chemistry, Medical University, 4A Chodźki Street, 20-093 Lublin, Poland |
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| Abstract: | Reaction of L-histidine with trifluoroacetaldehyde ethyl hemiacetal (TFAE) in boiling water provides 4-(trifluoromethyl)-L-spinacine, 4-(trifluoromethyl)-L-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid, in near quantitative yield. The product contains two diastereoisomers in the ratio 68 : 32. The isomers were separated (silica gel) as their protected derivatives, 5-N-(trifluoroacetyl)-4-(trifluoromethyl)-L-spinacine methyl esters, and were regenerated by acid hydrolysis. The analogous reaction with histamine provides 4-(trifluoromethyl)spinaceamine in 91% yield. |
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