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Synthesis 2002(15): 2165-2167
DOI: 10.1055/s-2002-34858
DOI: 10.1055/s-2002-34858
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Enantiopure N-(3,5-Dichlorophenyl)-2-hydroxysuccinimides (NDHS) and N-(3,5-Dichlorophenyl)-2-hydroxysuccinimide-O-sulfates (NSC)
Weitere Informationen
Received
14 June 2002
Publikationsdatum:
21. Oktober 2002 (online)
Publikationsverlauf
Publikationsdatum:
21. Oktober 2002 (online)
Abstract
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.
Key words
NDHS - NSC - enantiopure - nephrotoxicity - sulfate conjugates
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