| 3-(S)-巯基-1-(N-对硝基苄氧羰基乙酰亚胺)四氢吡咯的合成 |
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| 引用本文： | 李叶青,陆明,宋艳民,吕春绪. 3-(S)-巯基-1-(N-对硝基苄氧羰基乙酰亚胺)四氢吡咯的合成[J]. 化学试剂, 2006, 28(8): 493-495 |
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| 作者姓名： | 李叶青 陆明 宋艳民 吕春绪 |
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| 作者单位： | 南京理工大学,化工学院,江苏,南京,210094 |
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| 摘 要： | 对标题化合物的合成工艺作了改进。以L-羟基脯氨酸为原料,环己酮作催化剂,经脱羧获得的3-(R)-羟基四氢吡咯盐酸盐,与由乙醇和乙腈反应得到的乙氧基乙酰亚胺盐酸盐,经5步反应成功地合成了目标产物,总收率为15.6%,关键中间体及目标化合物经过1HNMR检测,还探讨了标题化合物及其前体的构型转化问题。
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| 关 键 词： | 3-(S)-巯基-1-(N-对硝基苄氧羰基乙酰亚胺)四氢吡咯 吡咯衍生物 合成 |
| 文章编号： | 0258-3283（2006）08-0493-03 |
| 收稿时间： | 2005-12-10 |
| 修稿时间： | 2005-12-10 |
Synthesis of 3-(S)-(+)-3-mercapto-1-(N-p-nitrobenzyloxycarbonyl acetimidoyl)pyrrolidine |
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| LI Ye-qing,LU Ming,SONG Yan-min,LU Chun-xu. Synthesis of 3-(S)-(+)-3-mercapto-1-(N-p-nitrobenzyloxycarbonyl acetimidoyl)pyrrolidine[J]. Chemical Reagents, 2006, 28(8): 493-495 |
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| Authors: | LI Ye-qing LU Ming SONG Yan-min LU Chun-xu |
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| Affiliation: | School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China |
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| Abstract: | To synthesize 3-(S)-( )-3-mercapto-1-(Np-nitrobenzyloxycarbonyl acetimidoyl)pyrrolidine,the main intermediates of Carbapenem RS-533 and its isomers and to improve the synthetic procedure,starting from L-hydroxyproline,in the presence of cyclohexanone as catalyst,3-(R)-(-)-3-hydroxypyrrolidine hydrochloride was prepared.Ethoxyacetimidate hydrochloride was prepared in high yield with alcohol and acetonitrile.Solid potassium thiolacetate was used to produce the target compound after five-step reaction,instead of sodium hydride and thiol-acetic acid.The key intermediates were analysized by(()~1HNMR).The conversions of configuration of the product and its intermediate were discussed in the article.The overall yield was 15.6%.This preparation method could be used industrially. |
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| Keywords: | 3-(S)-( )-3-mercapto-1-(N-p-nitrobenzyloxycarbonylacetimidoyl)pyrrolidine pyrrole derivative preparation |
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