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

Younas Aouine; Hassane Faraj; Anouar Alami; Abdelilah El-Hallaoui; Abdelrhani Elachqar; Abdelali Kerbal

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

Molecules. 2011 Apr 19;16(4):3380-90. doi: 10.3390/molecules16043380.

Authors

Younas Aouine¹, Hassane Faraj, Anouar Alami, Abdelilah El-Hallaoui, Abdelrhani Elachqar, Abdelali Kerbal

Affiliation

¹ Laboratoire de Chimie Organique Fès, Faculté des Sciences Dhar El Mahraz, Université Sidi Mohamed Ben Abdellah, Morocco.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Magnetic Resonance Spectroscopy
Mass Spectrometry
Stereoisomerism
Triazoles / chemical synthesis*
Triazoles / chemistry

Substances

Triazoles