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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
Resumen
MANCILLA PERCINO, Teresa y CRUZ HERNANDEZ, Teresita Rocío. Synthesis of Methyl-2[N-subtituted-N-(2-hydroxyethyl)]amino-2-hydroxyacetates and 2-Hydroxy-4-alkylperhydro-1,4-oxazin-3-ones. J. Mex. Chem. Soc [online]. 2007, vol.51, n.4, pp.185-192. ISSN 1870-249X.
This work describes the study of the reaction of methyl 2-hydroxy-2-methoxy acetate (1) with the β-amino alcohols, N-methylethanolamine (2), N-benzylethanolamine (3), (1R,2S)-(-)-ephedrine (4) and (1S,2S)-(+)-pseudoephedrine (5) in the presence of a mixture of benzene/ethanol and formic acid, and also without solvent. In the first case the reaction led to the new acyclic compounds methyl-2-[N-methyl-N-(2-hydroxyethyl)]amino-2-hydroxyacetate (2a), methyl-2[N-benzyl-N-(2-hydroxyethyl)]amino-2-hydroxyactetate (3a), methyl-2{N-methyl-N-[(2R,1S)-2-phenyl-1-methyl-2-hydroxyethyl]}amino-2-hydroxyacetates (4a, 4a') and methyl-2{N-methyl-N-[(2S,1S)-2-phenyl-1-methyl-2-hydroxyethyl]}amino-2-hydroxyacetates (5a, 5a'). The reaction without solvent led to cyclic compounds 2-hydroxy-4-methylperhydro-1,4-oxazin-3-ones (2b), 2- hydroxy-4-benzylperhydro-1,4-oxazin-3-one (3b), (2S,5S,6R)-2-hydroxy-4,5-dimethyl-6-phenylperhydro-1,4-oxazin-3-one (4b) and (2S,5S,6S)-2-hydroxy-4,5-dmiethyl-6-phenylperhydro-1,4-oxazin-3-one (5b), which we have been reported before, except 3b. The whole compounds were characterized by 1H, 13C, 15N (acyclic compounds) NMR, HETCOR, infrared and mass spectrometry. Determination of minimum energy of the preferred conformation was achieved for compounds 4a, 4a' , 5a and 5a' by theoretical calculation. The structures of 3b and 5b were further established by a single-crystal X-ray diffraction.
Palabras llave : 2-(N-hydroxyethylamino)hydroxyacetates; Oxazin-3-ones; Morpholin-3-ones; β-aminoalcohols; Spectroscopy; X-ray.