The determination of enantiomer composition of 1‐((3‐chlorophenyl)‐(phenyl)methyl) amine and 1‐((3‐chlorophenyl)(phenyl)‐methyl) urea (Galodif) by NMR spectroscopy, chiral HPLC, and polarimetry

The determination of enantiomer composition of 1‐((3‐chlorophenyl)‐(phenyl)methyl) amine and 1‐((3‐chlorophenyl)(phenyl)‐methyl) urea (Galodif) by NMR spectroscopy, chiral HPLC, and polarimetry

Bibliographische Detailangaben
Parent link:Chirality.— , 1999-
Vol. 30, iss. 10.— 2018.— [P.1135-1143]
Körperschaft: Национальный исследовательский Томский политехнический университет Инженерная школа новых производственных технологий Научно-образовательный центр Н. М. Кижнера
Weitere Verfasser: Kuksenok V. Yu. Vera Yurievna, Shtrykova V. V. Viktoriya Viktorovna, Filimonov V. D. Viktor Dmitrievich, Druganov A. G., Bondarev A. A. Aleksandr Aleksandrovich, Stankevich K. S. Ksenia Sergeevna
Zusammenfassung:Title screen
For the first time, a method for enantiomer resolution of the anticonvulsant Galodif (1‐((3‐chlorophenyl)(phenyl)methyl) urea) by chiral HPLC was developed, whereas the enantiomeric composition of 1‐((3‐chlorophenyl)(phenyl)methyl) amine-precursor in Galodif synthesis-cannot be resolved by this method. However, starting 1‐((3‐chlorophenyl)(phenyl)methyl) amine quantitatively forms diastereomeric N‐((3‐chlorophenyl)(phenyl)methyl)‐1‐camphorsulfonamides in reaction with chiral (1R)‐(+)‐ or (1S)‐(−)‐camphor‐10‐sulfonyl chlorides. The diastereomeric ratio of obtained camphorsulfonamides can be easily determined by NMR 1H and 13C spectroscopy. The DFT calculations of specific rotation of Galodif enantiomers showed good agreement with experimental data. The absolute configuration of enantiomers was proposed for the first time.
Режим доступа: по договору с организацией-держателем ресурса
Sprache:Englisch
Veröffentlicht: 2018
Schlagworte:
электронный ресурс
труды учёных ТПУ
anticonvulsants
chiral analysis
chiral HPLC
Galodif
NMR spectroscopy
polarimetry
specificrotation calculations
спектрометрия
поляриметрия
хиральность
Online-Zugang:https://doi.org/10.1002/chir.23005
Format: Elektronisch Buchkapitel
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=659009

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