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Synthesis of tritium, deuterium, and carbon‐14 labeled (S)‐N‐ethyl‐N‐methyl‐3‐[1‐(dimethylamino)ethyl]carbamic acid, phenyl ester, (L)‐2,3‐dihydroxybutanedioic acid salt (SDZ ENA 713 hta), an investigational drug for the treatment of Alzheimer's Disease
Author(s) -
Ciszewska Grazyna,
Pfefferkorn Heidi,
Tang Y. S.,
Jones Lawrence,
Tarapata Richard,
Sunay Ustun B.
Publication year - 1997
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199708)39:8<651::aid-jlcr14>3.0.co;2-8
Subject(s) - carbamic acid , chemistry , salt (chemistry) , deuterium , medicinal chemistry , stereochemistry , organic chemistry , physics , quantum mechanics
(S)‐(‐)‐ N ‐Ethyl‐ N ‐methyl‐3‐[1‐(dimethylamino)ethyl]carbamic acid, phenyl‐2‐ 3 H‐ester, (L)‐2,3‐dihydroxybutanedioic acid salt was synthesized via directed ortho ‐metallation methodology. (S)‐(‐)‐ N ‐Ethyl‐ N ‐methyl‐3‐[1‐(di‐( 2 H 3 )‐methylamino)ethyl]carbamic acid, phenyl ester, (L)‐2,3‐dihydroxybutanedioic acid salt was synthesized from 3‐hydroxyacetophenone. The molecule was resolved by classical diastereomeric salt formation and fractional crystallization. The carbon‐14 analog,(S)‐(‐)‐ N ‐Ethyl‐ N ‐methyl‐3‐[1‐(dimethylamino)ethyl‐1‐( 14 C)]carbamic acid, phenyl ester, (L)‐2,3‐dihydroxybutanedioic acid salt was constructed starting from 3‐iodoanisole and featured the enantioselective reduction of a methoxylamine intermediate. © John Wiley & Sons, Ltd.