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Trends in Organic Chemistry   Volumes    Volume 24 
Abstract
Convergent synthesis of N-(4-(3-ethoxy-2-hydroxypropyl)phenyl)-2-(methylthio) acetamide precursor of the suplatast tosylate
Margherita Colombo, Yousef Joqmara, Guillaume Pilet, Michele Fiore
Pages: 79 - 92
Number of pages: 14
Trends in Organic Chemistry
Volume 24 

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ABSTRACT
 
A novel, convergent synthesis with high yields of a known antiallergic compound precursor, the suplatast tosylate (±SN) is proposed. A deep analysis of the known chemical pathways prompted to explore convergent routes to increase yields and decrease production costs by using cheap and commercial starting materials. The intermediate N-(4-(3-ethoxy-2-hydroxypropyl)phenyl)-2-(methylthio) acetamide was obtained in 62% (linear) and 89% (convergent) overall yields with an improvement over the previously reported yields for the same compound. In addition, a complete 1H and 13C characterization is reported for all intermediates together with the x-ray structure of one of the key intermediates.
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