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- 中田 健也
- 東京理科大学理学部応用化学科
書誌事項
- タイトル別名
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- Development of Novel Methods for Preparing Chiral Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) by Asymmetric Esterification
- フセイ エステルカ ハンノウ ニ ヨル キラル ナ ヒステロイドセイ コウエンショウザイ(NSAIDs)ノ シンキ キョウキュウホウ ノ カイハツ
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A novel and efficient method for preparing chiral 2-arylalkanoic acid derivatives, including non-steroidal anti-inflammatory drugs (NSAIDs) such as ibuprofen, ketoprofen, fenoprofen, flurbiprofen, and naproxen, and their esters by asymmetric esterification is presented in this paper. A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic 2-arylalkanoic acids with achiral alcohols, using carboxylic anhydrides in the presence of chiral acyl-transfer catalysts. It was found that the combination of the modified benzotetramisole-type catalyst, (S)-β-Np-BTM, and a newly designed nucleophile, di(α-naphthyl)methanol, in the presence of a carboxylic anhydride, p-methoxybenzoic anhydride (PMBA) or pivalic anhydride (Piv2O), is most suitable for producing the corresponding chiral esters from 2-arylpropionic acid derivatives, with high enantiomeric excess under very mild reaction conditions. Using this new chiral acylation system, fairly broad substrate scope could be realized despite the multi-functional groups on the aromatic ring of the substrate. It was also revealed that ortho-substituted aromatic compounds, especially, 2,5-disubstituted aromatic ones were the most suitable compounds for providing a high selectivity.<br>
収録刊行物
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- 薬学雑誌
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薬学雑誌 132 (9), 993-1000, 2012-09-01
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
- 1390001206128540800
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- NII論文ID
- 130001888734
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- NII書誌ID
- AN00284903
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- COI
- 1:STN:280:DC%2BC3s%2Fht1CitA%3D%3D
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- ISSN
- 13475231
- 00316903
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- NDL書誌ID
- 023961643
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- PubMed
- 23023415
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- 本文言語コード
- ja
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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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- 使用不可