Automated synthesis of small molecules using chiral, non-racemic boronates
US9012658B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Apr 26, 2012 |
| Grant date | Apr 21, 2015 |
| Priority date | — |
| Expiry date | Apr 26, 2032 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2602/42
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Provided are methods for making and using chiral, non-racemic protected organoboronic acids, including pinene-derived iminodiacetic acid (PIDA) boronates, to direct and enable stereoselective synthesis of organic molecules. Also provided are methods for purifying PIDA boronates from solution. Also provided are methods for deprotection of boronic acids from their PIDA ligands. The purification and deprotection methods may be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chiral, non-racemic compounds. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated stereoselective synthesis of chiral, non-racemic small molecules using iterative cycles of deprotection, coupling, and purification.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.