Resumo

MANCILLA PERCINO, Teresa  e  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.

Palavras-chave : 2-(N-hydroxyethylamino)hydroxyacetates; Oxazin-3-ones; Morpholin-3-ones; β-aminoalcohols; Spectroscopy; X-ray.