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

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...

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Autores principales: Aouine, Younas, Faraj, Hassane, Alami, Anouar, El-Hallaoui, Abdelilah, Elachqar, Abdelrhani, Kerbal, Abdelali
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6260622/
https://www.ncbi.nlm.nih.gov/pubmed/21512446
http://dx.doi.org/10.3390/molecules16043380
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author Aouine, Younas
Faraj, Hassane
Alami, Anouar
El-Hallaoui, Abdelilah
Elachqar, Abdelrhani
Kerbal, Abdelali
author_facet Aouine, Younas
Faraj, Hassane
Alami, Anouar
El-Hallaoui, Abdelilah
Elachqar, Abdelrhani
Kerbal, Abdelali
author_sort Aouine, Younas
collection PubMed
description 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.
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spelling pubmed-62606222018-12-10 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 Aouine, Younas Faraj, Hassane Alami, Anouar El-Hallaoui, Abdelilah Elachqar, Abdelrhani Kerbal, Abdelali Molecules Article 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. MDPI 2011-04-19 /pmc/articles/PMC6260622/ /pubmed/21512446 http://dx.doi.org/10.3390/molecules16043380 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Aouine, Younas
Faraj, Hassane
Alami, Anouar
El-Hallaoui, Abdelilah
Elachqar, Abdelrhani
Kerbal, Abdelali
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6260622/
https://www.ncbi.nlm.nih.gov/pubmed/21512446
http://dx.doi.org/10.3390/molecules16043380
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