A Practical Procedure for the Synthesis of Esonarimod, (R,S)-2-Acetylthiomethyl-4-(4-methylphenyl)-4-oxobutanoic Acid, an Antirheumatic Agent. (Part 1).
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- Noguchi Toshiya
- Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd.
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- Onodera Akira
- Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd.
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- Tomisawa Kazuyuki
- Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd.
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- Yokomori Sadakazu
- Medicinal Research Laboratories, Taisho Pharmaceutical Co., Ltd.
書誌事項
- タイトル別名
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- Practical Procedure for the Synthesis of Esonarimod R S 2 Acetylthiomethyl 4 4 methylphenyl 4 oxobutanoic Acid an Antirheumatic Agent Part 1
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抄録
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.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 50 (10), 1407-1412, 2002
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679138382464
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- NII論文ID
- 110003615091
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- NII書誌ID
- AA00602100
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- COI
- 1:CAS:528:DC%2BD38XosFymtLo%3D
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 6313296
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- PubMed
- 12372877
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可