Method of preparing a derivative of optically active azetidin-2-one
US5712388A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | May 13, 1996 |
| Grant date | Jan 27, 1998 |
| Priority date | — |
| Expiry date | May 13, 2016 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F7/188
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
To prepare the compound (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one, (2S,3R)-2-aminomethyl-3-hydroxybutyric acid is reacted with an alcohol in the presence of at least one compound chosen from the group consisting of thionyl chloride, hydrogen chloride and p-toluene sulfonic acid, thereby obtaining a salt of the corresponding ester. The salt is reacted with a tri-substituted silane in the presence of a metallic catalyst, thereby protecting the hydroxy group of the ester and then reacted with a base, thereby obtaining an ester of (2S,3R)-2-aminomethyl-3-(tri-substituted silyloxy)butyric acid. Subsequently, the ester is transformed into lactam in the presence of a Grignard reagent or a metal amide, thereby obtaining (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one. This compound provides a useful base for preparing .beta.-lactam type antimicrobial agents such as carbapenem type agents.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.