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

Bibliografski detalji
Parent link:Chirality.— , 1999-
Vol. 30, iss. 10.— 2018.— [P.1135-1143]
Autor kompanije: Национальный исследовательский Томский политехнический университет Инженерная школа новых производственных технологий Научно-образовательный центр Н. М. Кижнера
Daljnji autori: 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
Sažetak: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
Izdano: 2018
Teme:
электронный ресурс
труды учёных ТПУ
anticonvulsants
chiral analysis
chiral HPLC
Galodif
NMR spectroscopy
polarimetry
specificrotation calculations
спектрометрия
поляриметрия
хиральность
Online pristup:https://doi.org/10.1002/chir.23005
Format: Elektronički Poglavlje knjige
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=659009
Opis
Sažetak: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
Digitalni identifikator objekta:10.1002/chir.23005

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