Experiment 27. Synthesis of an α,β-Unsaturated Carboxylic Acid Derivative, 348
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Synthesis of Albendazole Metabolite: Characterization and HPLC DeterminationGraciela Mahler, Danilo Davyt, Sandra Gordon, Marcelo Incerti, Ivana Núñez, Horacio Pezaroglo, Laura Scarone, Gloria Serra, Mauricio Silvera, and Eduardo Manta In this laboratory activity, students are introduced to the synthesis of an albendazole metabolite obtained by a sulfide oxidation reaction. Albendazole as well as its metabolite, albendazole sulfoxide, are used as anthelmintic drugs. The oxidation reagent is H2O2 in acetic acid. The reaction is environmental friendly, fast, and proceeds with high yield. The crude reaction is analyzed by HPLC chromatography to determine purity. The simplicity of the experiment allows students to study chiral concepts, physicochemical and spectroscopic properties of the compounds, and HPLC determinations. Mahler, Graciela; Davyt, Danilo; Gordon, Sandra; Incerti, Marcelo; Núñez, Ivana; Pezaroglo, Horacio; Scarone, Laura; Serra, Gloria; Silvera, Mauricio; Manta, Eduardo. J. Chem. Educ.2008, 85, 1652.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
HPLC |
Medicinal Chemistry |
Organosulfur Compounds |
Oxidation / Reduction |
Synthesis
The Discovery-Oriented Approach to Organic Chemistry. 7. Rearrangement of trans-Stilbene Oxide with Bismuth Trifluoromethanesulfonate and Other Metal TriflatesJames E. Christensen, Matthew G. Huddle, Jamie L. Rogers, Herbie Yung, and Ram S. Mohan Presents a microscale, green organic chemistry laboratory experiment that illustrates the utility of metal triflates, especially bismuth triflate, as a Lewis acid catalyst. Bismuth compounds are especially attractive for use as catalysts in organic synthesis because of their low toxicity, low cost, and ease of handling. Christensen, James E.; Huddle, Matthew G.; Rogers, Jamie L.; Yung, Herbie; Mohan, Ram S. J. Chem. Educ.2008, 85, 1274.
Catalysis |
Epoxides |
Green Chemistry |
Lewis Acids / Bases |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy
Isolation of Betulin and Rearrangement to AllobetulinBrian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen Betulin is obtained by extraction from birch bark and converted to allobetulin. Both compounds display 1H NMR spectra that include axialequatorial coupling characteristic of a C3-alcohol, conformational analysis by the use of dihedral angles and the Karplus equation, coupling patterns caused by diastereotopic protons and long-range interactions, and chemical shift values that are influenced by electronegativity and stereochemistry. Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. J. Chem. Educ.2007, 84, 1985.
