50624-94-7

Usage

Uses

Used in Chemical Synthesis:
Ethyl tert-Butyl Oxalate is used as a key intermediate in the synthesis of various organic compounds, particularly for the practical synthesis of functionalized 1,5-disubsituted 1,2,4-triazole derivatives. These derivatives are important in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals due to their diverse biological activities and potential applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl tert-Butyl Oxalate is used as a starting material for the synthesis of various drug candidates. The ability to form 1,5-disubsituted 1,2,4-triazole derivatives makes it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
Ethyl tert-Butyl Oxalate is also utilized in the agrochemical industry for the synthesis of novel compounds with potential pesticidal, herbicidal, or fungicidal properties. The 1,5-disubsituted 1,2,4-triazole derivatives formed from this ester can be further modified to enhance their bioactivity and selectivity, leading to the development of more effective and environmentally friendly agrochemicals.

InChI:InChI=1/C8H14O4/c1-5-11-6(9)7(10)12-8(2,3)4/h5H2,1-4H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 64-17-5 ethanol 
• 75-65-0 tert-butyl alcohol 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

• 50624-95-8 5-Benzyloxy-5-methyl-2-oxo-hex-3-ynoic acid tert-butyl ester 
• 35454-04-7 oxalamic Acid Tert-butyl Ester 
• 50624-99-2 2-(3-Benzyloxy-3-methyl-but-1-ynyl)-2-hydroxy-succinic acid 1-tert-butyl ester 4-ethyl ester 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 3422-01-3 tert-butyl phenylcarbamate 
• 4248-19-5 tert-butyl carbazate 
• 16466-61-8 1,2-bis(t-butyloxycarbonyl)hydrazine 
• 42116-43-8 tert-butyl 2-phenylhydrazine-1-carboxylate 
• 75716-84-6 tert-butyl 2-(4-methoxyphenyl)-2-oxoacetate 
• 1092464-37-3 tert-butyl 2-(3-cyanophenyl)-2-oxoacetate 
• 1257542-14-5 C₁₃H₂₁N₃O₂ 

Relevant academic research and scientific papers

Identification and Reactivity of s- cis, s- cis-Dihydroxycarbene, a New [CH2O2] Intermediate

We report the first preparation of the s-cis,s-cis conformer of dihydroxycarbene (1cc) by means of pyrolysis of oxalic acid, isolation of the lower-energy s-trans,s-trans (1tt) and s-cis,s-trans (1ct) product conformers at cryogenic temperatures in a N2 matrix, and subsequent narrow-band near-infrared (NIR) laser excitation to give 1cc. Carbene 1cc converts quickly to 1ct via quantum-mechanical tunneling with an effective half-life of 22 min at 3 K. The potential energy surface features around 1 were pinpointed by convergent focal point analysis targeting the AE-CCSDT(Q)/CBS level of electronic structure theory. Computations of the tunneling kinetics confirm the time scale of the 1cc → 1ct rotamerization and suggest that direct 1cc → H2 + CO2 decomposition may also be a minor pathway. The intriguing latter possibility cannot be confirmed spectroscopically, but hints of it may be present in the measured kinetic profiles.

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C?H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Cationic Chiral Pd-Catalyzed “Acetylenic” Diels–Alder Reaction: Computational Analysis of Reversal in Enantioselectivity

The highly enantioselective Diels–Alder reaction of acetylenic dienophiles is shown to be effectively catalyzed by cationic chiral palladium complexes. Not only the degree but also the sense of enantioselectivity critically depends on the steric demand of ligands. Computational analyses indicate that the steric demand does not affect the endo/exo-selectivity but the enantioface selectivity of dienes.

Practical synthesis of functionalized 1,5-disubstituted 1,2,4-triazole derivatives

A general approach for the synthesis of 1,5-disubstituted-1,2,4-triazole compounds is described. A series of new oxamide-derived amidine reagents can be accessed in excellent yield with minimal purification necessary. Typically, these amidine reagents are stable crystalline solids and in certain cases were found to exist in a cyclic form as determined by NMR spectroscopy. Under optimized conditions, the direct reaction of these prepared reagents with various hydrazine hydrochloride salts efficiently generates the target triazoles. Both aromatic and aliphatic hydrazines react readily with the amidine reagents under very mild reaction conditions, delivering desired 1,5-disubstituted-1,2,4-triazole derivatives in good yields.

O-alkyl hydroxamates as metaphors of enzyme-bound enolate intermediates in hydroxy acid dehydrogenases. Inhibitors of isopropylmalate dehydrogenase, isocitrate dehydrogenase, and tartrate dehydrogenase

The inhibition of Thermus thermophilus isopropylmalate dehydrogenase by O-methyl oxalohydroxamate was studied for comparison to earlier results of Schloss with the Salmonella enzyme. It is a fairly potent (1.2 μM), slow-binding, uncompetitive inhibitor against isopropylmalate and is far superior to an oxamide (25 mM Ki competitive) that is isosteric with the ketoisocaproate product of the enzyme. This improvement in inhibition was attributed to its increased NH acidity, which presumably is due to the inductive effect of the hydroxylamine oxygen. This principle was extended to the structurally homologous enzyme isocitrate dehydrogenase from E. coli, for which the compound O-(carboxymethyl) oxalohydroxamate is a 30 nM inhibitor, uncompetitive against isocitrate. The pH dependence of its inhibition supports the idea that it is bound to the enzyme in the anionic form. Another recently discovered homologous enzyme, tartrate dehydrogenase from Pseudomonas putida, was studied with oxalylhydroxamate. It has a relatively low affinity for the enzyme, though it is superior to tartrate. On the basis of these leads, squaric hydroxamates with increased acidity compared to squaric amides directed toward two of these enzymes were prepared, and they also show increased inhibitory potency, though not approaching the nanomolar levels of the oxalylhydroxamates.