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- W2153382009 abstract "This work describes the study of the reaction of methyl 2-hydroxy-2-methoxy acetate (1) with the b-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 com- pounds methyl-2-(N-methyl-N-(2-hydroxyethyl))amino-2-hydroxyac- etate (2a), methyl-2(N-benzyl-N-(2-hydroxyethyl))amino-2-hydroxy- actetate (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-dimethyl-6-phenylperhydro-1,4-oxazin-3- one (5b), which we have been reported before, except 3b. The whole compounds were characterized by 1 H, 13 C, 15 N (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 struc- tures of 3b and 5b were further established by a single-crystal X-ray" @default.
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- W2153382009 date "2007-12-01" @default.
- W2153382009 modified "2023-09-26" @default.
- W2153382009 title "Synthesis of Methyl-2[N-subtituted-N-(2-hydroxyethyl)]amino-2-hydroxyacetates and 2-Hydroxy-4-alkylperhydro-1,4-oxazin-3-ones" @default.
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