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Improved Synthesis and Crystallographic Analysis of (E)-Ethyl 2-(Hydroxyimino)-3-(4-methoxyphenyl)-3-oxopropanoate and erythro-N-Acetyl-b-(4-methoxyphenyl)serine Ethyl Ester
Corresponding Author(s) : S.X. Liu
Asian Journal of Chemistry,
Vol. 28 No. 1 (2016): Vol 28 Issue 1
Abstract
(E)-Ethyl 2-(hydroxyimino)-3-(4-methoxyphenyl)-3-oxopropanoate has been synthesized by the oximation of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate with ethyl nitrite in the presence of multi-pore activated-K2CO3. A one-pot procedure has also been developed for the conversion of this oxime to the corresponding erythro-2-acetamido-3-hydroxy-3-(4-methoxyphenyl)propionic ethyl ester. Their configurations were unambiguously confirmed by X-ray crystallographic determination. The oxime crystallized as a monoclinic system with space group P21/c and the following cell parameters: a = 11.524(3) Å, b = 7.2367(16) Å, c = 14.866(4) Å, b = 111.027(4) and Z = 4, whereas the erythro-N-acetyl-b-(4-methoxyphenyl)serine ethyl ester crystallized as a triclinic system with space group P-1 and the following cell parameters: a = 7.6451(6) Å, b = 13.3326(10) Å, c = 16.2679(13) Å, a = 67.314(7), b = 79.917(7), g = 88.516(7) and Z = 2. The crystal packing in both of these structures was stabilized by intermolecular O-H---O and C-H---O hydrogen bonds.
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- X.L. Li, X.L. Zhen, J.R. Han and S. Liu, J. Chem. Crystallogr., 39, 870 (2009); doi:10.1007/s10870-009-9581-5.
- N. Katagiri, H. Sato, A. Kurimoto, M. Okada, A. Yamada and C. Kaneko, J. Org. Chem., 59, 8101 (1994); doi:10.1021/jo00105a029.
- Y. Xie, A. Mi, Y. Jiang and H. Liu, Synth. Commun., 31, 2767 (2001); doi:10.1081/SCC-100105323.
- C. Mordant, P. Duenkelmann, V. Ratovelomanana-Vidal and J.-P. Genet, Chem. Commun., 1296 (2004); doi:10.1039/b401631a.
- O. Labeeuw, P. Phansavath and J.P. Genet, Tetrahedron Asymm., 15, 1899 (2004); doi:10.1016/j.tetasy.2004.05.004.
- C.E. Humphrey, M. Furegati, K. Laumen, L. La Vecchia, T. Leutert, J.C.D. Müller-Hartwieg and M. Vögtle, Org. Process Res. Dev., 11, 1069 (2007); doi:10.1021/op700093y.
- C.J. Barrow, M.S. Doleman, M.A. Bobko and R. Cooper, J. Med. Chem., 37, 356 (1994); doi:10.1021/jm00029a007.
- S. Pohle, C. Appelt, M. Roux, H.-P. Fiedler and R.D. Süssmuth, J. Am. Chem. Soc., 133, 6194 (2011); doi:10.1021/ja108971p.
- H. Inoue, K. Matsuki and T. Ohishi, Chem. Pharm. Bull. (Tokyo), 41, 1521 (1993); doi:10.1248/cpb.41.1521.
- G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
- Y.T. Chang and W.H. Hartung, J. Am. Chem. Soc., 75, 89 (1953); doi:10.1021/ja01097a025.
References
X.L. Li, X.L. Zhen, J.R. Han and S. Liu, J. Chem. Crystallogr., 39, 870 (2009); doi:10.1007/s10870-009-9581-5.
N. Katagiri, H. Sato, A. Kurimoto, M. Okada, A. Yamada and C. Kaneko, J. Org. Chem., 59, 8101 (1994); doi:10.1021/jo00105a029.
Y. Xie, A. Mi, Y. Jiang and H. Liu, Synth. Commun., 31, 2767 (2001); doi:10.1081/SCC-100105323.
C. Mordant, P. Duenkelmann, V. Ratovelomanana-Vidal and J.-P. Genet, Chem. Commun., 1296 (2004); doi:10.1039/b401631a.
O. Labeeuw, P. Phansavath and J.P. Genet, Tetrahedron Asymm., 15, 1899 (2004); doi:10.1016/j.tetasy.2004.05.004.
C.E. Humphrey, M. Furegati, K. Laumen, L. La Vecchia, T. Leutert, J.C.D. Müller-Hartwieg and M. Vögtle, Org. Process Res. Dev., 11, 1069 (2007); doi:10.1021/op700093y.
C.J. Barrow, M.S. Doleman, M.A. Bobko and R. Cooper, J. Med. Chem., 37, 356 (1994); doi:10.1021/jm00029a007.
S. Pohle, C. Appelt, M. Roux, H.-P. Fiedler and R.D. Süssmuth, J. Am. Chem. Soc., 133, 6194 (2011); doi:10.1021/ja108971p.
H. Inoue, K. Matsuki and T. Ohishi, Chem. Pharm. Bull. (Tokyo), 41, 1521 (1993); doi:10.1248/cpb.41.1521.
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
Y.T. Chang and W.H. Hartung, J. Am. Chem. Soc., 75, 89 (1953); doi:10.1021/ja01097a025.