Process for the stereospecific preparation of 5-(1-hydroxy-2-urethanethylidene)-2,-dimethyl-1,3-dioxane-4,6-dione derivatives, which are precursors of chiral tetramic acid derivatives
US5498732A · kind A · utility
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10Claims
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Key dates
| Filing date | Sep 15, 1994 |
| Grant date | Mar 12, 1996 |
| Priority date | — |
| Expiry date | Sep 15, 2014 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D319/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The invention relates to a process for the preparation of 5-(1-hydroxy-2-urethanethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives, which are precursors of chiral tetramic acid derivatives. According to this process, an N-urethane-protected .alpha.-amino acid N-carboxy-anhydride is reacted with Meldrum's acid in an inert organic solvent medium in the presence of a tertiary amine. This process makes it possible to conserve the chirality of the starting material and in particular to simplify the synthesis of 4-amino-3-hydroxy acids and the derivatives thereof via the tetramic acid route.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.