Synthesis, phase behavior and absolute configuration of β-adrenoblocker bupranolol and related compounds
Abstract
β-Blocker bupranolol 1, it's hydrochloride and their precursors 1-(2-chloro-5-methylphenoxy)-2,3-epoxypropane 2 and 3-(2-chloro-5-methylphenoxy)propane-1,2-diol 3 were prepared in racemic and single-enantiomer forms. For all the studied compounds phase behavior during crystallization was established on the basis of IR, DSC and X-ray investigations. Absolute configurations were established for compounds 1 and 2. Being conglomerate, racemic oxirane 2 was resolved by direct entrainment procedure. Being anticonglomerate, in the process of recrystallization, almost enantiopure 1·HCl accumulates in the mother liquor, not in the crystalline precipitate.
- Publication:
-
Journal of Molecular Structure
- Pub Date:
- December 2018
- DOI:
- 10.1016/j.molstruc.2018.06.079
- Bibcode:
- 2018JMoSt1173..157B
- Keywords:
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- Chiral drug bupranolol;
- Phase behavior;
- Single crystal X-ray analysis;
- Conglomerate and anticonglomerate