Method for preparing the enantiomerized concentrated form of 3-(2-chlorothiazole-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-A]pyrimidine-4-ium-5-oleate.
An economical process using a chiral transition metal catalyst and activator enhances the production of enantiomer-enriched 3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-4-ium-5-olate, improving selectivity and yield over existing cumbersome and costly methods.
Patent Information
- Application Number
- JP2023544051
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Priority Date
- 2021-01-22
- Filing Date
- 2022-01-21
- Publication Date
- 2026-04-06
- Estimated Expiration
- 2042-01-21
AI Technical Summary
Existing methods for preparing 3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-4-ium-5-oleate and its enantiomerized forms are cumbersome, costly, and yield unsatisfactory, with inefficient use of reagents and multiple reaction steps.
A method involving the reduction of 2-[2-(2-chlorothiazol-5-yl)-2-oxo-ethyl]sulfanyl-6-hydroxy-3-methyl-5-phenyl-pyrimidin-4-one in the presence of a chiral transition metal catalyst and a reducing agent, followed by reaction with an activator to enhance electrophilicity without racemization, resulting in an enantiomer-enriched form of 3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate.
The method achieves high selectivity and economic production of enantiomer-enriched forms of the compound, addressing the inefficiencies of previous methods by reducing costs and improving yield.