Chiral synthesis of alpha-aminophosponic acids
US5362899A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Sep 9, 1993 |
| Grant date | Nov 8, 1994 |
| Priority date | — |
| Expiry date | Sep 9, 2013 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F9/4006
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A stereospecific method of preparing alpha-aminophosphonic acids and derivatives thereof is provided. A protected amino acid is converted to a acyl aroyl or diacyl peroxide which spontaneously rearranges to form an alpha-amino ester. This rearrangement occurs stereospecifically with retention of configuration. The ester is subsequently converted to an appropriate leaving group and displaced with a phosphite yielding a chiral alpha-aminophosphonic acid or derivative. Alpha-aminophosphonic acids are useful for the synthesis of peptide analogs that possess a phosphonate linkage in the place of an amide linkage. This substitution can impart protease resistance in therapeutic peptides thereby increasing the serum half-life.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.