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Synthesis of EnantiopureN-(3,5-Dichlorophenyl)-2-hydroxysuccinimides (NDHS) andN-(3,5-Dichlorophenyl)-2-hydroxysuccinimide-O-sulfates (NSC)
Synthesis ( IF 2.2 ) Pub Date : 2002-01-01 , DOI: 10.1055/s-2002-34858
Gary O. Rankin , Hang Sun , Bryson McCain , John L. Hubbard , Minghui Chai

Enantiomerically pure N-(3,5-dichlorophenyl)-2-hydroxysuccinimides (NDHS) and N-(3,5-dichlorophenyl)-2-hy­droxysuccinimide-O-sulfates (NSC) have been synthesized in our laboratory in order to address their selectively related nephrotoxic mechanism. The key step for NDHS synthesis is the intramolecular nucleophilic cyclization via the amide N-atom with retention of configuration of the original stereogenic center. The corresponding sulfate conjugates (R)-NSC and (S)-NSC were prepared by reaction of enantiomeric NDHS with chlorosulfonic acid at -78 °C.

中文翻译:

对映体纯 N-(3,5-二氯苯基)-2-羟基琥珀酰亚胺 (NDHS) 和 N-(3,5-二氯苯基)-2-羟基琥珀酰亚胺-O-硫酸盐 (NSC) 的合成

我们实验室合成了对映体纯的 N-(3,5-二氯苯基)-2-羟基琥珀酰亚胺 (NDHS) 和 N-(3,5-二氯苯基)-2-羟基琥珀酰亚胺-O-硫酸盐 (NSC),以解决它们的问题。选择性相关的肾毒性机制。NDHS 合成的关键步骤是通过酰胺 N 原子进行分子内亲核环化,同时保留原始立体中心的构型。相应的硫酸盐缀合物 (R)-NSC 和 (S)-NSC 通过对映体 NDHS 与氯磺酸在 -78 °C 下反应制备。
更新日期:2002-01-01
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