Esters of (2-hydroxy-3-oxo-cyclopent-1-enyl) acetic acid and their use for preparing (−)-R-homocitric acid gamma-lactone, (+)-S-homocitric acid gamma-lactone and the corresponding (−)-R-homocitric acid and (+)-S-homocitric acid salts
US8148568B2 · kind B2 · utility
Assignees
Inventors
Key dates
| Filing date | May 25, 2007 |
| Grant date | Apr 3, 2012 |
| Priority date | — |
| Expiry date | Feb 2, 2029 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2601/10
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Archiral (2-hydroxy-3-oxo-cyclopent-1-enyl) acetic acid) alkyl, alkylphenyl and phenyl esters, and a simple and efficient method for the synthesis of both enantiomers of homocitric acid gamma-lactone and the corresponding salts from these esters are described. The method is based on asymmetric oxidation of esters, and the steps of basic and acidic hydrolysis and final acidic lactonization of the homocitric acid into homocitric acid gamma-lactone. The homocitric acid salts are obtained after basic treatment of homocitric acid gamma-lactone. The esters, conditions and reagents used in chemical conversion and separating products are important constituents affording efficient and simple method for production of homocitric acid gamma-lactone and homocitric acid salts.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.