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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Main Authors:	Abdelali Kerbal, Abdelrhani Elachqar, Anouar Alami, Abdelilah El-Hallaoui, Younas Aouine, Hassane Faraj
Format:	Article
Language:	English
Published:	MDPI AG 2011-04-01
Series:	Molecules
Subjects:	oxazoline 1H-1,2,4-triazole high regioselective alkylation β‑aminoalcohol β‑(1,2,4-triazol-1-yl)alanine
Online Access:	http://www.mdpi.com/1420-3049/16/4/3380/

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spelling	doaj-3e42fa9c9cb84fb8950af6f2a0ea7ebf2020-11-24T20:46:23ZengMDPI AGMolecules1420-30492011-04-011643380339010.3390/molecules16043380Simple 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)alanineAbdelali KerbalAbdelrhani ElachqarAnouar AlamiAbdelilah El-HallaouiYounas AouineHassane FarajA 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.http://www.mdpi.com/1420-3049/16/4/3380/oxazoline1H-1,2,4-triazolehigh regioselective alkylationβ‑aminoalcoholβ‑(1,2,4-triazol-1-yl)alanine
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Abdelali Kerbal Abdelrhani Elachqar Anouar Alami Abdelilah El-Hallaoui Younas Aouine Hassane Faraj
spellingShingle	Abdelali Kerbal Abdelrhani Elachqar Anouar Alami Abdelilah El-Hallaoui Younas Aouine Hassane Faraj 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 oxazoline 1H-1,2,4-triazole high regioselective alkylation β‑aminoalcohol β‑(1,2,4-triazol-1-yl)alanine
author_facet	Abdelali Kerbal Abdelrhani Elachqar Anouar Alami Abdelilah El-Hallaoui Younas Aouine Hassane Faraj
author_sort	Abdelali Kerbal
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_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_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_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
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2011-04-01
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.
topic	oxazoline 1H-1,2,4-triazole high regioselective alkylation β‑aminoalcohol β‑(1,2,4-triazol-1-yl)alanine
url	http://www.mdpi.com/1420-3049/16/4/3380/
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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

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