55304-19-3

Usage

Uses

Used in Pharmaceutical Industry:
(2,6-DIMETHYLPHENOXY)ACETOXIME is used as a metabolite for Mexiletine, an antiarrhythmic drug, for the treatment of various cardiac arrhythmias. Its presence in the body is a result of the metabolism of Mexiletine, and it contributes to the overall therapeutic effects of the drug.
Used in Research and Development:
(2,6-DIMETHYLPHENOXY)ACETOXIME is also used as a research compound in the development of new drugs and therapies related to cardiac arrhythmias. Its unique chemical structure and properties make it a valuable tool for understanding the mechanisms of action and potential side effects of Mexiletine and other related compounds.
Used in Quality Control and Analysis:
In the pharmaceutical industry, (2,6-DIMETHYLPHENOXY)ACETOXIME is used as a reference compound for quality control and analysis of Mexiletine and its formulations. It helps ensure the purity, potency, and consistency of the drug, which is crucial for its effectiveness and safety in treating patients with cardiac arrhythmias.

Upstream product

• 53012-41-2 (2,6-dimethylphenoxy)-2-propanone 
• 576-26-1 2.6-dimethylphenol 
• 102588-22-7 N,N-bis(trimethylsilyloxy)-1-propen-2-amine 

Relevant academic research and scientific papers

Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals

The regioselectivity of the addition of HO-acids to the activated π bond in N,N-bis(oxy)enamines has been found to be dramatically dependent upon the solvent. Mechanistic investigations and quantum-chemical calculations revealed that solvent affects the reaction pathway. In basic solvents (DMF, NMP, DMSO), N,N-bis(oxy)enamines were converted into nitrosoalkenes by a Lewis base promoted process followed by oxy-Michael addition of the HO-acid. In non-polar solvents (toluene, CH2Cl2), the reaction occurs by an acid-promoted SN′ substitution of the N-oxy-group via a highly reactive N-vinyl-N-alkoxynitrenium species. Based on these studies, general and efficient protocols for the oximinoalkylation of various HO-acids (carboxylic acids, phenols, hydroxamic, phosphoric and sulfonic acids) employing readily available N,N-bis(oxy)enamines were developed. These methods proved to be applicable to the post-modification of natural molecules bearing acidic OH groups (such as steroidal hormones, bile acids, protected amino acids and peptides) and ligands (BINOL). The resulting α-oxyoximes were demonstrated to be useful precursors of valuable 1,2-amino alcohol or 1,2-hydroxylamino alcohol derivatives, including the antiarrhythmic drug Mexiletine and a potent matrix metalloproteinase inhibitor.

A practical and efficient route for the highly enantioselective synthesis of mexiletine analogues and novel β-thiophenoxy and pyridyl ethers

(Chemical Equation Presented) A practical and efficient procedure for the enantioselective synthesis of mexiletine analogues with use of 10% of spiroborate ester 6 as chirality transfer agent is presented. A variety of mexiletine analogues were prepared in good yield with excellent enantioselectivities (91-97% ee) from readily available starting materials. The developed methodology was also successfully applied for the synthesis of novel β-amino ethers containing thiophenyl and pyridyl fragments.