Simple and Efficient Synthesis of Racemic 2-(tert-Butoxycarbon-ylamino)-2-methyl-3-(1H-1,2,4-triazol-1-yl)propanoic Acid, a New Derivative of β-(1,2,4-Triazol-1-yl)alanine

Abstract

A simple synthetic approach to racemic N-tert-butyloxycarbonyl-2-methyl-3-(1H-1,2,4-triazol-1-yl)alanine (5) in four steps and 68% overall yield starting from oxazoline derivative 1 is reported. This synthesis involves the alkylation of 1H-1,2,4-triazole with an O-tosyloxazoline derivative, followed by an oxazoline ring-opening reaction and oxidation of the N-protected β‑aminoalcohol by potassium permanganate.

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

“…In continuation of our research interest in heterocyclic amino acids and their precursors [13][14][15][16][17][18], we report in the present study our results concerning the synthesis and antibacterial activity of a new 1,2,3-triazole compound, as diethyl 1-((4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate, an oxazolinic precursor of heterocyclic amino acids via 1,3-dipolar cycloaddition reaction between 2-phenyl-4-methyl-4-(azidomethyl)oxazoline and diethyl but-2-ynedioate. The synthesized triazole derivative was characterized by spectroscopic techniques, such as 1D and 2D NMR spectroscopy, mass spectrometry (MS), and X-ray crystallography.…”

4,4-Bis(hydroxymethyl)-2-phenyl-2-oxazoline

“…The oxazoline ring has low reactivity towards nucleophiles, radicals, oxidizing agents, and acids, and is used in applications requiring high chemical resistance [6,7]; they are also widely used as linkers in asymmetric catalysis [8], monomeric building blocks [9,10], and ligands in cross-coupling reactions [11,12]. Continuing our investigations in the use of oxazoline in heterocyclic chemistry [13][14][15][16][17] we describe in this short note our results concerning the resynthesis of 4,4-bis(hydroxymethyl)-2-phenyl-2-oxazoline (CAS No. [62203-32-1]) [18][19][20][21][22][23][24], an oxazolinic precursor of biheterocyclic amino acids.…”

4-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole

“…In the continuation of our research concerning heterocyclic amino acids and their precursors [10][11][12][13][14], we described in this short note our results concerning the synthesis of a new pyrazole compound, 4-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-methyl-2-phenyl-4,5-dihydrooxazole, an oxazolinic precursor of heterocyclic amino acids via nucleophilic substitution reaction of the (4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl-4-methylbenzenesulfonate and the 3,5-dimethyl-1H-pyrazole. The title compound was characterized by spectroscopic techniques, such as 1D and 2D NMR spectroscopy, mass spectrometry (MS) and elemental analysis.…”