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    • 7. 发明授权
    • Method for producing β-alaninamides
    • β-丙氨酰胺生产方法
    • US06878829B2
    • 2005-04-12
    • US10220608
    • 2001-03-02
    • Stefan HildbrandThomas RuppenDario Veghini
    • Stefan HildbrandThomas RuppenDario Veghini
    • C07C231/14C07C237/12C07C255/19C07D207/337C07D233/54C07D233/60C07D233/64
    • C07D233/64C07C231/14C07C255/19Y02P20/55C07C237/12
    • 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.
    • 通式为β-丙烯酰胺,其中R 1为氢或未被取代或被羟基,氨基,羧基,氨基甲酰基,甲基巯基,胍基,未取代或取代的芳基或杂芳基取代的C 1-6烷基,R 2为氢 ,或R 1和R 2一起形成式 - (CH 2)n - 的基团,其中n为3或4,R 3为氢,负电荷由当量的无机或 通过使相应的α-氨基酸或相应的α-氨基酸酯与氰基乙酸酯反应得到氰基乙酰胺,然后通过随后的催化氢化制备无需氨基保护基团的有机阳离子或C 1-6烷基。 该方法特别适用于制备肌肽(β-丙氨酰-L-组氨酸,R 1 =咪唑-4-基 - 甲基,R 2 = R 3 = H),天然存在的二肽,其用作 一种具有抗氧化作用的膳食补充剂。