Method for producing β-alaninamides
US6878829B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Mar 2, 2001 |
| Grant date | Apr 12, 2005 |
| Priority date | — |
| Expiry date | May 2, 2021 |
Classification
- Technology area (CPC Y)Emerging Cross-Sectional Technologies
- CPC primaryY02P20/55
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
β-alaninamides of the general formula Wherein R1 is hydrogen or C1-6 alkyl which is unsubstituted or substituted with hyroxy, amino, carboxy, carbamoyl, methylmercapto, guanidino, unsubstituted or substituted aryl or heteroaryl, and R2 is hydrogen, or R1 and R2 together form a group of the formula —(CH2)n— where n is 3 or 4, and R3 is hydrogen, a negative charge compensated by an equivalent of an inorganic or organic cation or is C1-6 alkyl, are prepared, without using an amino-protective group, by reacting the corresponding α-amino acid or the corresponding α-amino acid ester with a cyanoacetic ester to give a cyanoacetamide and by subsequent catalytic hydrogenation. The method is particularly suitable for preparing carnosine (β-alanyl-L-histidine, R1=imidazol-4-yl-methyl, R2=R3=H), a naturally occurring dipeptide which used as a dietary supplement with antioxidative action.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.