Convenient Cleavage Reaction of 1-Acylhydantoin to Amide

DOI: 10.4236/ijoc.2013.33025   PDF   HTML   XML   3,933 Downloads   5,796 Views  


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.

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J. Yamaguchi, K. Abe and T. Narushima, "Convenient Cleavage Reaction of 1-Acylhydantoin to Amide," International Journal of Organic Chemistry, Vol. 3 No. 3, 2013, pp. 194-197. doi: 10.4236/ijoc.2013.33025.

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[1] 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
[2] 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
[3] 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
[4] 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
[5] 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
[6] 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
[7] 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
[8] 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
[9] 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
[10] 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
[11] D. J. Porubek, H. Barnes, L. J. Theodore and T. A. Baillie, “Enantioselective Synthesis and Primary Metabolic Studies of the Optical Isomers of 2-n-Propyl-4-pentanoic Acid, a Hepatotoxic Metabolite of Valproic Acid,” Chemical Research in Toxicology, Vol. 1, No. 6, 1988, pp. 343-348. doi:10.1021/tx00006a004
[12] M. T. Crimmins, D. M. Bankaitis-Davis and W. G. Hollis, Jr., “Total Synthesis of Milbemycin β3,” The Journal of Organic Chemistry, Vol. 53, No. 3, 1988, pp. 652-657. doi:10.1021/jo00238a031
[13] M. T. Crimmins and R. O’Mahony, “A Synthesis of (-)Talaromycin A,” The Journal of Organic Chemistry, Vol. 54, No. 5, 1989, pp. 1157-1161. doi:10.1021/jo00266a030
[14] C. Santini, R. G. Bal and G. D. Berger, “Absolute Stereochemistry of the Squalene Synthase Inhibitor Zaragozic Acid C,” The Journal of Organic Chemistry, Vol. 59, No. 8, 1994, pp. 2261-2266. doi:10.1021/jo00087a054
[15] T. D. Penning, S. W. Djuric, R. A. Haack, V. J. Kalish, J. M. Miyashiro, B. W. Rowell and S. S. Yu, “Improved Procedure for the Reduction of N-Acyloxazolidinones,” Synthetic Communications, Vol. 20, No. 2, 1990, pp. 307-312. doi:10.1080/00397919008052299
[16] A. Orita, Y. Nagano, J. Hirano and J. Otera, “Lewis AcidPromoted Transesterification of N-Acyl Oxazolidinones under Mild Conditions,” Synlett, No. 5, 2001, pp. 637-639.
[17] D. A. Evans, H. P. Ng and D. L. Rieger, “Total Synthesis of the Macrolide Antibiotic Rutamycin B,” Journal of the American Chemical Society, Vol. 115, No. 24, 1993, pp. 11446-11459. doi:10.1021/ja00077a049
[18] V. Rodeschini, P. Van de Weghe, C. Tarnus and J. Eustache, “A Simple Spiroepoxide as Methionine Aminopeptidase-2 Inhibitor: Synthetic Problems and Solutions,” Tetrahedron Letters, Vol. 46, No. 39, 2005, pp. 6691-6695. doi:10.1016/j.tetlet.2005.07.136
[19] T. K. Jones, R. A. Reamer, R. Desmond and S. G. Mills, “Chemistry of Tricarbonyl Hemiketals and Application of Evan’s Technology to the Total Synthesis of the Immunosuppressant (-)-FK-506,” Journal of the American Chemical Society, Vol. 112, No. 8, 1990, pp. 2998-3017. doi:10.1021/ja00164a023
[20] J. Yamaguchi, M. Harada, T. Kondo, T. Noda and T. Suyama, “A Facile Method for Preparation of Optically Active Hydantoin,” Chemistry Letters, Vol. 32, No. 4, 2003, pp. 372-373. doi:10.1246/cl.2003.372
[21] J. Yamaguchi, M. Harada, T. Narushima, A. Saitoh, K. Nozaki and T. Suyama, “Diastereoselective Conjugate Addition of 1-(α,β-Unsaturated acyl)hydantoin with Nucleophiles,” Tetrahedron Letters, Vol. 46, No. 38, 2005, pp. 6411-6415. doi:10.1016/j.tetlet.2005.07.116
[22] K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, J. Sugimori, “Asymmetric Diels-Alder Reaction by a Chiral Titanium Reagent,” Journal of the American Chemical Society, Vol. 111, No. 14, 1989, pp. 5340-5345. doi:10.1021/ja00196a045

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