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
Vera Yu Kuksenok
1
,
Victoria V Shtrykova
1
,
Victor D. Filimonov
1
,
Alexandr G Druganov
2
,
Alexandr A Bondarev
3
,
K. Stankevich
1
Publication type: Journal Article
Publication date: 2018-08-03
scimago Q2
wos Q1
SJR: 0.682
CiteScore: 4.9
Impact factor: 3.0
ISSN: 08990042, 1520636X
PubMed ID:
30075486
Catalysis
Organic Chemistry
Drug Discovery
Spectroscopy
Pharmacology
Analytical Chemistry
Abstract
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 1 H and 13 C 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.
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Kuksenok V. Yu. et al. 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 // Chirality. 2018. Vol. 30. No. 10. pp. 1135-1143.
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Kuksenok V. Yu., Shtrykova V. V., Filimonov V. D., Druganov A. G., Bondarev A. A., Stankevich K. 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 // Chirality. 2018. Vol. 30. No. 10. pp. 1135-1143.
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TY - JOUR
DO - 10.1002/chir.23005
UR - https://doi.org/10.1002/chir.23005
TI - 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
T2 - Chirality
AU - Kuksenok, Vera Yu
AU - Shtrykova, Victoria V
AU - Filimonov, Victor D.
AU - Druganov, Alexandr G
AU - Bondarev, Alexandr A
AU - Stankevich, K.
PY - 2018
DA - 2018/08/03
PB - Wiley
SP - 1135-1143
IS - 10
VL - 30
PMID - 30075486
SN - 0899-0042
SN - 1520-636X
ER -
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@article{2018_Kuksenok,
author = {Vera Yu Kuksenok and Victoria V Shtrykova and Victor D. Filimonov and Alexandr G Druganov and Alexandr A Bondarev and K. Stankevich},
title = {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},
journal = {Chirality},
year = {2018},
volume = {30},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/chir.23005},
number = {10},
pages = {1135--1143},
doi = {10.1002/chir.23005}
}
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Kuksenok, Vera Yu., et al. “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.” Chirality, vol. 30, no. 10, Aug. 2018, pp. 1135-1143. https://doi.org/10.1002/chir.23005.