An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization
A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation,...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/5375670 |
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| author | Qi Liao Lan Jiang Cong Li Yaling Shen Min Wang Chengkun Cao Xiangnan Hu |
| author_facet | Qi Liao Lan Jiang Cong Li Yaling Shen Min Wang Chengkun Cao Xiangnan Hu |
| author_sort | Qi Liao |
| collection | DOAJ |
| description | A mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate. |
| format | Article |
| id | doaj-art-f03a72335a9e475688b5e6adbce8a039 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-f03a72335a9e475688b5e6adbce8a0392025-02-03T05:52:55ZengWileyJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/53756705375670An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its OptimizationQi Liao0Lan Jiang1Cong Li2Yaling Shen3Min Wang4Chengkun Cao5Xiangnan Hu6Department of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaCollege of Environment and Resources, Chongqing Technology and Business University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaDepartment of Medicinal Chemistry, Pharmacy School, Chongqing Medical University, Chongqing, ChinaA mild and relatively simple way for preparation of 2-(3-hydroxy-1-adamantane)-2-oxoacetic acid (I) was reported. It was prepared from 1-adamantanecarboxylic acid (II) via sulfuric acid/nitric acid to get 3-hydroxy-1-adamantanecarboxylic acid (III); treated with the one-pot method through acylation, condensation, and decarboxylation to obtain 3-hydroxy-1-acetyladamantane (IV); and finally oxidized by potassium permanganate (KMnO4) to get the target compound (I). The overall yield was about 60%, which provides a new idea for commercial production of saxagliptin intermediate.http://dx.doi.org/10.1155/2019/5375670 |
| spellingShingle | Qi Liao Lan Jiang Cong Li Yaling Shen Min Wang Chengkun Cao Xiangnan Hu An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization Journal of Chemistry |
| title | An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization |
| title_full | An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization |
| title_fullStr | An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization |
| title_full_unstemmed | An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization |
| title_short | An Efficient and Practical Method for the Synthesis of Saxagliptin Intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic Acid and Its Optimization |
| title_sort | efficient and practical method for the synthesis of saxagliptin intermediate 2 3 hydroxy 1 adamantane 2 oxoacetic acid and its optimization |
| url | http://dx.doi.org/10.1155/2019/5375670 |
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