Premium
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
Author(s) -
Kuksenok Vera Yu.,
Shtrykova Victoria V.,
Filimonov Victor D.,
Druganov Alexandr G.,
Bondarev Alexandr A.,
Stankevich Ksenia S.
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23005
Subject(s) - chemistry , diastereomer , enantiomer , amine gas treating , chiral column chromatography , nuclear magnetic resonance spectroscopy , chirality (physics) , absolute configuration , chiral derivatizing agent , specific rotation , urea , spectroscopy , stereochemistry , medicinal chemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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 (1 R )‐(+)‐ or (1 S )‐(−)‐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.