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, iss. 10
| Parent link: | Chirality.— , 1999- Vol. 30, iss. 10.— 2018.— [P.1135-1143] |
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| Institution som forfatter: | |
| Andre forfattere: | , , , , , |
| Summary: | 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 |
| Sprog: | engelsk |
| Udgivet: |
2018
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| Fag: | |
| Online adgang: | https://doi.org/10.1002/chir.23005 |
| Format: | Electronisk Book Chapter |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=659009 |
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| 200 | 1 | |a 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 |f V. Yu. Kuksenok [et al.] | |
| 203 | |a Text |c electronic | ||
| 300 | |a Title screen | ||
| 320 | |a [References: 43 tit.] | ||
| 330 | |a 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. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | 1 | |t Chirality |d 1999- | |
| 463 | 1 | |t Vol. 30, iss. 10 |v [P.1135-1143] |d 2018 | |
| 610 | 1 | |a электронный ресурс | |
| 610 | 1 | |a труды учёных ТПУ | |
| 610 | 1 | |a anticonvulsants | |
| 610 | 1 | |a chiral analysis | |
| 610 | 1 | |a chiral HPLC | |
| 610 | 1 | |a Galodif | |
| 610 | 1 | |a NMR spectroscopy | |
| 610 | 1 | |a polarimetry | |
| 610 | 1 | |a specificrotation calculations | |
| 610 | 1 | |a спектрометрия | |
| 610 | 1 | |a поляриметрия | |
| 610 | 1 | |a хиральность | |
| 701 | 1 | |a Kuksenok |b V. Yu. |c chemist |c Senior Lecturer of Tomsk Polytechnic University, Candidate of Chemical Sciences |f 1989- |g Vera Yurievna |3 (RuTPU)RU\TPU\pers\32463 |9 16412 | |
| 701 | 1 | |a Shtrykova |b V. V. |c chemist |c Associate professor of Tomsk Polytechnic University, Candidate of chemical sciences |f 1962- |g Viktoriya Viktorovna |3 (RuTPU)RU\TPU\pers\31887 |9 15959 | |
| 701 | 1 | |a Filimonov |b V. D. |c Russian chemist |c Professor of the TPU |f 1945- |g Viktor Dmitrievich |3 (RuTPU)RU\TPU\pers\26423 |9 12127 | |
| 701 | 1 | |a Druganov |b A. G. | |
| 701 | 1 | |a Bondarev |b A. A. |g Aleksandr Aleksandrovich | |
| 701 | 1 | |a Stankevich |b K. S. |c Physicist |c Engineer Tomsk Polytechnic University |f 1992- |g Ksenia Sergeevna |3 (RuTPU)RU\TPU\pers\37546 | |
| 712 | 0 | 2 | |a Национальный исследовательский Томский политехнический университет |b Инженерная школа новых производственных технологий |b Научно-образовательный центр Н. М. Кижнера |3 (RuTPU)RU\TPU\col\23556 |
| 801 | 2 | |a RU |b 63413507 |c 20181221 |g RCR | |
| 856 | 4 | |u https://doi.org/10.1002/chir.23005 | |
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