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
Open Access
- 19 April 2011
- Vol. 16 (4) , 3380-3390
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
This publication has 21 references indexed in Scilit:
- Synthesis and Crystal Structure of Novel Sulfone Derivatives Containing 1,2,4-Triazole MoietiesMolecules, 2010
- Synthesis, antifungal activity and CoMFA analysis of novel 1,2,4-triazolo[1,5-a]pyrimidine derivativesEuropean Journal of Medicinal Chemistry, 2008
- Synthesis of novel triazole derivatives as inhibitors of cytochrome P450 14α-demethylase (CYP51)European Journal of Medicinal Chemistry, 2007
- Synthesis and antimicrobial activities of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines carrying thioalkyl and sulphonyl phenoxy moietiesEuropean Journal of Medicinal Chemistry, 2007
- Synthesis and antibacterial activity of 1-[1,2,4-triazol-3-yl] and 1-[1,3,4-thiadiazol-2-yl]-3-methylthio-6,7-dihydrobenzo[c]thiophen-4(5H)onesBioorganic & Medicinal Chemistry Letters, 2005
- Synthesis, antitumor and antiviral properties of some 1,2,4-triazole derivativesIl Farmaco, 2004
- Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl)piperazinyl quinolone derivativesIl Farmaco, 2003
- Resolution, Absolute Stereochemistry, and Pharmacology of the S-(+)- and R-(-)-Isomers of the Apparent Partial AMPA Receptor Agonist (R,S)-2-Amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic Acid [(R,S)-APPA]Journal of Medicinal Chemistry, 1994
- Enzymic synthesis of non-protein β-substituted alanines and some higher homologues in plantsPhytochemistry, 1994
- Tetrazole amino acids as competitive NMDA antagonistsBioorganic & Medicinal Chemistry Letters, 1993