Method for producing β-alaninamides

Details Method for producing β-alaninamides Method for producing β-alaninamides

2005-04-12

2005-04-12

Stockton, Laura L. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S338100, C548S339100

Reexamination Certificate

active

06878829

ABSTRACT:
β-alaninamides of the general formulaWherein R1is hydrogen or C1-6alkyl which is unsubstituted or substituted with hyroxy, amino, carboxy, carbamoyl, methylmercapto, guanidino, unsubstituted or substituted aryl or heteroaryl, and R2is hydrogen, or R1and R2together form a group of the formula —(CH2)n— where n is 3 or 4, and R3is hydrogen, a negative charge compensated by an equivalent of an inorganic or organic cation or is C1-6alkyl, 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.

REFERENCES:
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Nishi, CA 93:168588, 1980.*
Copy of International Search Report and Preliminary Examination Report from applicants' corresponding International (PCT) Patent Application, Apr. 11, 2002.
Norman, R.O.C., “Principles of Organic Synthesis”, (1968), Methuen & Co. Ltd. Science Paperbacks, London, p. 572.

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