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

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

1
Laboratoire de Chimie Organique Fès, Faculté des Sciences Dhar El Mahraz, Université Sidi Mohamed Ben Abdellah, Morocco
2
Centre Universitaire Régional d’Interface (CURI), Université Sidi Mohamed Ben Abdellah, Fès, Morocco
*
Author to whom correspondence should be addressed.
Received: 15 March 2011 / Revised: 7 April 2011 / Accepted: 11 April 2011 / Published: 19 April 2011
(This article belongs to the Section Organic Synthesis)
Download PDF [390 KB, 18 June 2014; original version 18 June 2014]

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 oxazoline; 1H-1,2,4-triazole; high regioselective alkylation; β‑aminoalcohol; β‑(1,2,4-triazol-1-yl)alanine
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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