Method for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones
US6613919B2 · kind B2 · utility
Assignee
Inventor
Key dates
| Filing date | Jun 28, 2002 |
| Grant date | Sep 2, 2003 |
| Priority date | — |
| Expiry date | Jun 28, 2022 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D307/60
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
This invention affords a solution to the technical problem of obtaining one or both enantiomers of 5-substituted 4-hydroxyfuran-2-ones in pure form by resolution with enantiomerically pure bases. Racemic mixtures of 5-substituted 4-hydroxy-2(5H)-furanones, including 5-substituted and 5,5-disubstituted, 4-hydroxy and 3,4-dihydroxy furanones are separated into pure enantiomers by crystallization with an enantiomerically pure base, such as cinchonidine. In specific solvent mixtures, for example, 95% ethanol, the diastereomerically pure salt of one enantiomer crystallizes. The enantiomerically pure furanone can then be obtained simply by filtration and treatment of the salt with an acid, for example, trifluoracetic acid, followed by precipitation with water, filtration and drying. Moreover, the other enantiomer may be equally obtained in pure form by evaporation of the mother liquor, followed by the same treatment of the salt as described before.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.