A facile stereospecific synthesis of the [2H6]-isopropyl-labelled metoprolol enantiomers from (2r)- and (2S)-glycidyl 3-nitrobenzenesulfonate
| Autor: | Satya S. Murthy, Wendel L. Nelson |
|---|---|
| Rok vydání: | 1990 |
| Předmět: |
Organic Chemistry
Biochemistry High-performance liquid chromatography Medicinal chemistry Analytical Chemistry chemistry.chemical_compound Stereospecificity Deuterium chemistry Drug Discovery medicine Phenol Organic chemistry Radiology Nuclear Medicine and imaging Enantiomer Enantiomeric excess Spectroscopy Isopropyl Metoprolol medicine.drug |
| Zdroj: | Journal of Labelled Compounds and Radiopharmaceuticals. 28:1411-1416 |
| ISSN: | 0362-4803 |
| DOI: | 10.1002/jlcr.2580281208 |
| Popis: | Enantiomers of metoprolol containing six deuterium atoms in the isopropyl methyl groups were prepared in two steps from the sodium salt of 4-(2-methoxyethyl)phenol (3) and the commercially available (2R)- and (2S)-glycidyl 3-nitrobenzenesulfonates [(2R)-2 and (2S)-2]. The resulting (2R)- and (2S)-epoxides were opened using [2H6]-isopropylamine. The enantiomeric excesses were 93 and 95% for the deuterated (2R)- and (2S)-enantiomers of metoprolol [(2R)-1 and (2S)-1], respectively, as determined by chiral column HPLC. |
| Databáze: | OpenAIRE |
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