Tert-butyl esters of 2,3-diaryl-3-arylaminopropanoic acids - stereoselective synthesis, isolation, spectroscopic and structural elucidation

Open access

Tert-butyl esters of 2,3-diaryl-3-arylaminopropanoic acids - stereoselective synthesis, isolation, spectroscopic and structural elucidation

A series of seven substituted tert-butyl esters of 2,3-diaryl-3-arylaminopropanoic acids has been synthesized, isolated, spectroscopically and structurally elucidated. An influence of the substituents on the spectroscopic characteristics and conformations is discussed using the data of the linear-polarized IR- (IR-LD), UV-spectroscopy and 1H-NMR. Theoretical quantum chemical calculations are carried out, with a view to explaining and supporting the experimental optical properties and the electronic structure. The stereoselective synthesis of the corresponding diastereoisomers is optimized, thus giving good yields (62-72%) and purity of the compounds

Drey, C.N. (1985). In Barret G. S. (Ed.), Chemistry and Biochemistry of the Amino Acids (1 st ed.), London, Chapman & Hall.

Liu, M. & Sibi, M. (2002). Recent advances in the stereoselective synthesis of β-amino acids. Tetrahedron 58(40), 7991-8035. DOI: 10.1016/S0040-4020(02)00991-2.

Periasamy, M., Suresh, S. & Ganesan, S. (2005). Stereoselective synthesis of syn-β-amino esters using the TiCl4/R3N reagent system. Tetrahedron Lett. 46(33), 5521-5524. DOI:10.1016/j.tetlet.2005.06.048.

Krauthauser, S., Christianson, L., Powell, D. & Gellman, S. (1997). Antiparallel sheet formation in β-peptide foldamers: Effects of β-amino acid substitution on conformational preference. J. Am. Chem. Soc. 119(48), 11719-11720. DOI: 10.1021/ja9730627.

Kise, N., Ueda, N. (1999). A new method for the synthesis of β-amino acid derivatives and β-lactams. Reaction of N-alkoxycarbonyl-1-methoxyamines with esters. J. Org. Chem. 64(20), 7511-7514. DOI: 10.1021/jo990821q.

Escalante, J., Guanzales-Tototzin, M., Avina, J., Minoz-Miniz, O. & Juaristi, E. (2001). Synthesis of β-lactams and cyclo-β-dipeptides from β-amino acids: experimental observations and theoretical analysis. Tetrahedron, 57(10), 1883-1890. DOI:10.1016/S0040-4020(00)01169-8.

Taggi, A., Havez, A. & Lectka, T. (2003). α-Imino esters: Versatile substrates for the catalytic, asymmetric synthesis of α- and β-amino acids and β-lactams. Acc. Chem. Res. 36(1), 10-19. DOI: 10.1021/ar020137p.

Rosenblum, S., Huynh, T., Afonso, A., Davis, H., Yumibe, N., Clader, J. & Burnett, D. (1998). Discovery of 1-(4-Fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235): A Designed, Potent, Orally Active Inhibitor of Cholesterol Absorption. J. Med. Chem. 41(6), 973-980. DOI: 10.1021/jm970701f.

Koleva, B., Kolev, T., Seidel, R., Spiteller, M., Mayer-Figge, H. & Sheldrick, W. (2009). Self-assembly of hydrogensquarates: Crystal structures and properties. J. Phys. Chem. A 113(13), 3088-3095. DOI: 10.1021/jp8106233.

Koleva, B., Kolev, T., Seidel, R., Mayer-Figge, H., Spiteller, M. & Sheldrick, W. (2008). On the origin of the color in the solid state. Crystal structure and optical and magnetic properties of 4-Cyanopyridinium hydrogensquarate monohydrate. J. Phys. Chem. A. 112(13), 2899-2905. DOI: 10.1021/jp710765v.

Koleva, B.B, Kolev, T.M., Simeonov, V., Spassov, T. & Spiteller, M. (2008) Linearly polarized IR-spectroscopy of partially oriented solids as a colloid suspension in nematic host: A tool for spectroscopic and structural elucidation of the embedded chemicals. J. Incl. Phen. Macro. 61, 319-333. DOI: 10.1007/s10847-008-9425-5.

Koleva, B.B., Kolev, T., Mayer-Figge, H., Seidel, R.W., Spiteller, M. & Sheldrick, W.S. (2008) Are there preferable conformations of the tryptammonium cation in the solid state? Crystal structure and solid-state linear polarized IR-spectroscopic study of tryptammonium hydrogentartarate Struct. Chem. 19, 147-154. DOI: 10.1007/s11224-007-9265-8.

Ivanova, B. & Spiteller, M. (2010). Noncentrosymmetric crystals with marked nonlinear optical properties. J. Phys. Chem. A. 114(15), 5099-5103. DOI: 10.1021/jp1002758.

Ivanova, B. & Spiteller, M. (2010). Possible application of the organic barbiturates as NLO materials. Cryst. Growth Des. 10(6), 2470-2474. DOI: 10.1021/cg100284r.

Kolev, T., Koleva, B., Seidel, R., Spiteller, M. & Sheldrick, W. (2009). New aspects on the origin of color in the solid state. Coherently shifting of the protons in violurate crystals. Cryst. Growth Des. 9(8), 3348-3352. DOI: 10.1021/cg900188k.

Ivanova, B. & Spiteller, M. (2010). Conformations and properties of the L-tryptophyl-containing peptides in solution, depending on the pH-theoretical study vs. experiments. Biopolymers 93(8), 727-734. DOI: 10.1002/bip.21437.

Ivanova, B. & Spiteller, M. (2010). Organic mandelates as promising materials with non-linear optical application. Struct. Chem. 21(5), 989-993. DOI 10.1007/s11224-010-9635-5.

Frisch, M.J. Trucks, G.W. Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Zakrzewski, V.G., Montgomery Jr., J.A., Stratmann, R.E., Burant, J.C., Dapprich, S., Millam, J.M.; Daniels, A.D., Kudin, K.N., Strain, M.C., Farkas, Ö., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P.Y., Cui, Q., Morokuma, K., Salvador, P., Dannenberg, J.J., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J.V., Baboul, A. G., Stefanov, B.B., Liu, G.; Liashenko, A., Piskorz, P., Komáromi, I., Gomperts, R., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Andres, J.L., Gonzalez, C., Head-Gordon, M., Replogle, E. S. & Pople, J. A. Gaussian 98, Gaussian, Inc., Pittsburgh, PA, 1998.

Becke, A.D. (1993). Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98(7), 5648-5652. DOI: 10.1063/1.464913.

Becke, A.D. (1996). Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing. J. Chem. Phys. 104(3), 1040-1046. DOI:10.1063/1.470829.

Lee, C., Yang, W. & Parr, R.G. (1988). Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37(2), 785-789. DOI: 10.1103/PhysRevB.37.785.

Scott, P. & Radom, L. (1996). Harmonic Vibrational Frequencies: An Evaluation of Hartree-Fock, Moller-Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors. J. Phys. Chem. 100(41), 16502-16513. DOI: 10.1021/jp960976r.

DeFrees D.J. & McLean, A.D. (1985). Molecular orbital predictions of the vibrational frequencies of some molecular ions. J. Chem. Phys. 82(1), 333-341. DOI:10.1063/1.448805.

Dryanska, V.D., Tasheva, D.N. & Ivanov, Ch. Ch. (1992). Phase transfer catalyzed additions IX. Influence of the reaction conditions on the reaction of tert-butyl phenylacetate with benzylideneaniline. Bulg. Chem. Commun. 26(1), 66-73.

Spassov, S.L. (1971). Nuclear magnetic resonance spectra, configuration and conformation of diastereomers-II: Ethyl esters of 3-substituted 2,3-diphenylpropanoic acids: Magnetic nonequivalence induced by two asymmetric centres. Tetrahedron 27(6), 1323-1329. DOI:10.1016/S0040-4020(01)90883-X.

Kolev, T., Preut, H., Bleckmann, P. & Juchnovski, I. (1995). (+/-)-Threo-3-Hydroxy-2,3-diphenylpropanoic acid methyl ester Acta Crystallogr. C. 51, 1350-1352. DOI:10.1107/S0108270194014277.

Kolev, T., Preut, H., Bleckmann, P. & Juchnovski, I. (1995). (+/-)-Threo-3-Hydroxy-2,3-diphenylpropanoic acid dimethylamide. Acta Crystallogr. C. 51, 1169-1170. DOI:10.1107/S0108270194014666.

Polish Journal of Chemical Technology

The Journal of West Pomeranian University of Technology, Szczecin

Journal Information


IMPACT FACTOR 2018: 0,975
5-year IMPACT FACTOR: 0,878

CiteScore 2018: 1

SCImago Journal Rank (SJR) 2018: 0.269
Source Normalized Impact per Paper (SNIP) 2018: 0.46

Metrics

All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 272 190 7
PDF Downloads 74 53 4