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

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 39, Issue 8, 1997, Pages 651-668

  Ciszewska, Grazyna ^a   Pfefferkorn, Heidi ^a   Tang, Y S ^a,b   Jones, Lawrence ^a   Tarapata, Richard ^a   Sunay, Ustun B ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Acetylcholine esterase inhibitor; Alzheimer's disease; Carbon 14; Deuterium; Directed ortho metalation; Enantioselective reduction.; Tritium

Indexed keywords

CARBON; ENANTIOSELECTIVITY; ESTERS; NEURODEGENERATIVE DISEASES; ORGANIC ACIDS; TRITIUM;

ACETYLCHOLINE ESTERASE; ACETYLCHOLINE ESTERASE INHIBITOR; ACID SALTS; ALZHEIMERS DISEASE; CARBAMIC ACID; CARBON 14; DIRECTED ORTHO-METALATION; ENANTIOSELECTIVE REDUCTION; ENANTIOSELECTIVE REDUCTION.; PHENYL ESTERS;

DEUTERIUM;

CARBON 14; CHOLINESTERASE INHIBITOR; DEUTERIUM; RIVASTIGMINE; TRITIUM;

ARTICLE; CRYSTALLIZATION; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; ISOTOPE LABELING; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

ENA; TRITIUM;

EID: 0030853920     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1344(199708)39:8<651::AID-JLCR14>3.0.CO;2-8     Document Type: Article

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35. It is interesting to note that compound 19 would not give a crystalline salt with (L)-tartaric acid while there was >6-7 % of the undesired (R)-enantiomer of the amine present in the mixture. This is the reason why direct purification and enantiomeric purification of the 9:1 (S):(R) mixture of 19 to enantiopure 4 could not be undertaken.
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