- 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
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(S)-(-)-N-Ethyl-N-methyl-3-[1-(dimethylamino)ethyl] carbamic acid, phenyl-2-3H-ester, (L)-2,3-dihydroxybutanedioic acid salt was synthesized via directed ortho-metallation methodology. (S)-(-)-N-Ethyl-N-methyl-3-[1-(di-(2H3)-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-(14C)]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.
- Ciszewska, Grazyna,Pfefferkorn, Heidi,Tang,Jones, Lawrence,Tarapata, Richard,Sunay, Ustun B.
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