| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346522 | Tetrahedron: Asymmetry | 2016 | 7 Pages |
The solubility of the chiral drug bevantolol hydrochloride1 in water and the azeotropic mixture ethanol–water has been investigated. It was found that rac-1 meets the requirements of Meyerhoffer’s rule, so it was possible to reduce the ternary diagram, describing the solubility of 1, to a pseudo binary form, which facilitates the analysis of crystallization processes caused by temperature changes. On this basis, the effective and robust resolution procedure of racemic bevantolol hydrochloride by a preferential crystallization approach has been realized successfully.
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(R)-1-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]-3-(3-methylphenoxy)-2-propanolC20H28ClNO4Ee = 99.8% (ee from HPLC)[α]D20 = +19.3 (c 1.1, EtOH)Initial source of chirality: resolution of racemic 1-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-3-(3-methylphenoxy)-2-propanol by preferential crystallizationAbsolute configuration: (R)
(R)-1,2-Epoxy-3-(2-methylyphenoxy)propaneC10H12O2[α]D20 = −12.9 (c 1.0, MeOH)Initial source of chirality: (S)-epichlorohydrinAbsolute configuration: (R)
