Next Article in Journal
Previous Article in Journal
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

1, 1, 1,* , 1, 1 and 1,2
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)
Download PDF [390 KB, updated 18 June 2014; original version uploaded 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


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.



Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert