Study on the Deprotection of Boc Group of S-2-(tert-Butoxycarbonylamino)ethyl 3-Phenylpropanethioates
文献类型：期刊论文
| 作者 | Jia Yaoling1; Wang Yang1,2 |
| 刊名 | CHINESE JOURNAL OF ORGANIC CHEMISTRY
 |
| 出版日期 | 2011-04 |
| 卷号 | 31期号:4页码:538-543 |
| 关键词 | S-2-(tert-butoxycarbonylamino)ethyl 3-phenylpropanethioate thiazoline Boc group trifluoroacetic acid (TFA) |
| ISSN号 | 0253-2786 |
| 文献子类 | Article |
| 英文摘要 | S-2-(tert-Butoxycarbonylamino)ethyl 3-phenylpropanethioates (3a similar to 3d) were synthesized in 79%similar to 92% yields through the esterification of substituted 3-phenylpropanoic acids (1a similar to 1d) and methyl N-(tert-butoxycarbonyl)-L-cysteine (2) by using bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-Cl) as the condensation agent. The deprotection of Boc group of 3a similar to 3d by trifluoroacetic acid (TFA) gave not only normal deprotecting products 4a similar to 4d but also 2-substituted thiazolines 5a similar to 5d which were obtained by intramolecular dehydration of the corresponding 4a similar to 4d, whereas the deprotection of Boc group of S-2-(tert-butoxycarbonylamino)ethyl 3-phenylpropenethioates (3e similar to 3f) afforded only deprotecting products 4e similar to 4f under the same condition due to their double bond rigid structures. 4a similar to 4d and 5a similar to 5d could be obtained in high yields (85%similar to 91% and 86%similar to 89%) respectively by optimizing reaction conditions on the amount of TFA, the reaction temperature and time, which provided a facile and effective method to synthesize 2-substituted thiazolines. |
| WOS关键词 | THIAZOLINES |
| WOS研究方向 | Chemistry |
| 语种 | 中文 |
| WOS记录号 | WOS:000290468100015 |
| 出版者 | SCIENCE PRESS |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/278559]  |
| 专题 | 新药研究国家重点实验室 中科院受体结构与功能重点实验室 |
| 通讯作者 | Jia Yaoling |
| 作者单位 | 1.Fudan Univ, Dept Med Chem, Sch Pharm, Shanghai 201203, Peoples R China; 2.Chinese Acad Sci, State Key Lab Drug Res, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Jia Yaoling,Wang Yang. Study on the Deprotection of Boc Group of S-2-(tert-Butoxycarbonylamino)ethyl 3-Phenylpropanethioates[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY,2011,31(4):538-543. |
| APA | Jia Yaoling,&Wang Yang.(2011).Study on the Deprotection of Boc Group of S-2-(tert-Butoxycarbonylamino)ethyl 3-Phenylpropanethioates.CHINESE JOURNAL OF ORGANIC CHEMISTRY,31(4),538-543. |
| MLA | Jia Yaoling,et al."Study on the Deprotection of Boc Group of S-2-(tert-Butoxycarbonylamino)ethyl 3-Phenylpropanethioates".CHINESE JOURNAL OF ORGANIC CHEMISTRY 31.4(2011):538-543. |
入库方式： OAI收割
来源：上海药物研究所
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