Paper
Study on the Synthesis of 4-Methyl-5-formylthiazole
Published 2009 · Su Wei-ke
Journal of Chemical Engineering of Chinese Universities
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Abstract
4-Methyl-5-formylthiazole (1), a key intermediate for the synthesis of Cefditoren Pivoxil, was synthesized from methyl 3-oxobutanoate (2) via three steps. The first step is the α-bromination of substrate 2, followed by condensation with thiourea to afford methyl 2-amino-4-methylthiazole-5-carboxylate (3) with 96% yield; the second step is diazotization-reduction of compound 3 by using cheaper sodium phosphenite (1.5 equiv) in place of phosphonous acid, and the key intermediate methyl 4-methylthiazole-5-carboxylate (4) was obtained with 75% yield. The third step is the reduction of ester 4 by potassium borohydride/lithium chloride system (1.5 equiv) under reflux ethanol, followed by oxidation using sodium chlorite (2.0 equiv) in the presence of TEMPO under mild condition to provide the target compound 1 with 62% yield. The total yield is over 44% and the advantages of the present procedure are easy operation, mild reaction condition and high yield, so it can be expected to have a good prospect for industrial application.
The study presents a three-step method for synthesizing 4-Methyl-5-formylthiazole, a key intermediate in Cefditoren Pivoxil, with high yield and easy operation, making it suitable for industrial application.
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