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A Practical Procedure for the Synthesis of Esonarimod, (R,S)-2-Acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic Acid, an Antirheumatic Agent. Part 1
- Source :
- ChemInform. 34
- Publication Year :
- 2003
- Publisher :
- Wiley, 2003.
-
Abstract
- An efficient and practical procedure for the synthesis of esonarimod, (R,S)-2-acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic acid (1), a new antirheumatic drug, has been developed. The intermediate, 2-methylene-4-(4-methylphenyl)-4-oxobutanoic acid (2), was prepared by Friedel-Crafts acylation of toluene with itaconic anhydride (3) in the presence of aluminum trichloride and nitrobenzene in 63% yield without silica gel column purification. Compound 1 was prepared by Michael addition of 2 with thioacetic acid (4) in 74% yield. Overall, 1 was obtained in 47% yield from 3. The structures and synthetic mechanisms of by-products (five compounds) of 2 were also clarified.
- Subjects :
- chemistry.chemical_classification
Phenylpropionates
Silica gel
Carboxylic acid
General Chemistry
General Medicine
4-(4-Methylphenyl)-4-oxobutanoic acid
Thioester
Chemical synthesis
Toluene
Medicinal chemistry
Acylation
Nitrobenzene
chemistry.chemical_compound
chemistry
Antirheumatic Agents
Yield (chemistry)
Drug Discovery
Michael reaction
Thioacetic acid
Subjects
Details
- ISSN :
- 15222667 and 09317597
- Volume :
- 34
- Database :
- OpenAIRE
- Journal :
- ChemInform
- Accession number :
- edsair.doi.dedup.....c2f91f2c283359a3c1fa5b5cf915b4b2