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Convenient Cleavage Reaction of 1-Acylhydantoin to Amide
Department of Applied Chemistry, Kanagawa Institute of Technology, Kanagawa, Japan
Department of Applied Chemistry, Kanagawa Institute of Technology, Kanagawa, Japan
Department of Applied Chemistry, Kanagawa Institute of Technology, Kanagawa, Japan
- 1 Department of Applied Chemistry, Kanagawa Institute of Technology, Kanagawa, Japan
- 2 Department of Applied Chemistry, Kanagawa Institute of Technology, Kanagawa, Japan
- 3 Department of Applied Chemistry, Kanagawa Institute of Technology, Kanagawa, Japan
International Journal of Organic Chemistry·Volume 03 (2013)·Pages 194–197·Published 27 August 2013·DOI10.4236/ijoc.2013.33025
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Abstract
A cleavage reaction of 1-acylhydantoin by an amine in tetrahydrofuran at elevated temperature provided the corre-sponding amide and hydantoin in high yield. It was found that the addition of diethylaluminum chloride accelerated the cleavage reaction rate. The amide yield depended on the steric hindrance of the amine.
KeywordsAmidesAcylhydantoinChiral AuxiliariesCleavageLewis Acid
- D. A. Evans and D. J. Mathre, “Asymmetric Synthesis of the Enkephalinase Inhibitor Thiorpan,” The Journal of Organic Chemistry, Vol. 50, No. 11, 1985, pp. 1830-1835. doi:10.1021/jo00211a008
- W. H. Miles, P. M. Smiley and H. R. Brinkman, “The Reaction of Chiral Nucleophiles with Organomanganese Arene Complex,” Journal of the Chemical Society, Chemical Communications, No. 24, 1989, pp. 1897-1899. doi:10.1039/c39890001897
- D. A. Evans, R. L. Dow, T. L. Shih, J. M. Takacs, R. Zahler, “Total Synthesis of the Polyether Antibiotic Ionomycin,” Journal of the American Chemical Society, Vol. 112, No. 13, 1990, pp. 5290-5313. doi:10.1021/ja00169a042
- D. L. J. Clive, K. S. K. Murthy, A. G. H. Wee, J. S. Prasad, G. V. J. da Silva, M. Majewski, P. C. Anderson, C. F. Evans, R. D. Haugen, L. D. Heerze and J. R. Barrie, “Total Synthesis of Both (+)-Compactins. A General Strategy Based on the Use of a Special Titanium Reagent for Dicarbonyl Coupling,” Journal of the American Chemical Society, Vol. 112, No. 8, 1990, pp. 3018-3028. doi:10.1021/ja00164a024
- D. A. Evans, T. C. Britton and J. A. Ellman, “Contrasteric Carboximide Hydrolysis with Lithium Hydroperoxide,” Tetrahedron Letters, Vol. 28, No. 49, 1987, pp. 6141-6144. doi:10.1016/S0040-4039(00)61830-0
- M. Nakano, S. Atsuumi, Y. Koike, S. Tanaka, H. Funabashi, J. Hashimoto, M. Ohkubo and H. Morishima, “Synthesis of a Homostatine-Containing Renin Inhibitor Which Incorporates a Sulfonemethylene Isostere at Its N-Terminus,” Bulletin of Chemical Society of Japan, Vol. 63, No. 8, 1990, pp. 2224-2232. doi:10.1246/bcsj.63.2224
- M. Trova, R. E. Babine, R. A. Byrn, W. T. Casscles, Jr., R. C. Hastings, G. C. Hsu, M. R. Jirousek, B. D. Johnson, S. S. Kerwar, S. R. Schow, A. Wissner, N. Zhang and M. M. Wick, “Synthesis and Biological Evaluation of a Series of HIV-1 Protease Inhibitors,” Bioorganic and Medicinal Chemistry Letters, Vol. 3, No. 8, 1993, pp. 1595-1600. doi:10.1016/S0960-894X(00)80024-4
- P. E. Sonnet and R. R. Heath, “Aryl Substituted Diastereomeric Alkenes: Gas Chromatographic Behavior on a Non-polar Versus a Liquid Crystal Phase,” Journal of Chromatography, Vol. 321, 1985, pp. 127-136. doi:10.1016/S0021-9673(01)90429-7
- D. F. Taber, E. H. Petty and K. Raman, “Enantioselective Ring Construction: Synthesis of (+)-α-Cuparenone,” Journal of the American Chemical Society, Vol. 107, No. 1, 1985, pp. 196-199. doi:10.1021/ja00287a035
- R. E. Zelle, M. P. DeNinno, H. G. Selnick and S. J. Danishefsky, “A Systematic Degradation of Zincophorin: A Stereoselective Synthesis of the C17-C-25 Fragment,” The Journal of Organic Chemistry, Vol. 51, No. 25, 1986, pp. 5032-5036. doi:10.1021/jo00375a060