Molecules 2011, 16(4), 3380-3390; doi:10.3390/molecules16043380
Article

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

Received: 15 March 2011; in revised form: 7 April 2011 / Accepted: 11 April 2011 / Published: 19 April 2011
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
Keywords: oxazoline; 1H-1,2,4-triazole; high regioselective alkylation; β‑aminoalcohol; β‑(1,2,4-triazol-1-yl)alanine
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MDPI and ACS Style

Aouine, Y.; Faraj, H.; Alami, A.; El-Hallaoui, A.; Elachqar, A.; Kerbal, A. 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. Molecules 2011, 16, 3380-3390.

AMA Style

Aouine Y, Faraj H, Alami A, El-Hallaoui A, Elachqar A, Kerbal A. 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. Molecules. 2011; 16(4):3380-3390.

Chicago/Turabian Style

Aouine, Younas; Faraj, Hassane; Alami, Anouar; El-Hallaoui, Abdelilah; Elachqar, Abdelrhani; Kerbal, Abdelali. 2011. "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." Molecules 16, no. 4: 3380-3390.

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