📄 详细内容
合成路线:Compound can be prepared in two different ways:1) The reaction of N-trifluoroacetyl-L-glutamic acid 1-ethyl ester-5-acid chloride (I) with diazomethane in ether gives 6-diazo-5-oxonorleucine ethyl ester (II),which can be hydrolyzed by treatment with ammonia or NaOH in ethanol water.2) The hydrogenation of gamma-benzyl ester of N-carboxy-L-glutamate anhydride (III) with H2 over Pd/C in ethyl acetate gives N-carboxy-L-glutamate anhydride (IV),which by reaction with refluxing SOCl2 yields L-4-[2-(chlorocarbonyl)ethyl]oxazolidine-2,5-dione (V).The reaction of (V) with diazomethane in ether affords L-4-(4-diazo-3-oxobutyl)oxazolidine-2,5-dione (VI),which is finally hydrolyzed with NaOH in water at room temperature.
参考文献标题:
文献作者:Moore,A.M.; de Wald,H.A.
参考来源:US 2878245
合成路线:Compound can be prepared in two different ways:1) The reaction of N-trifluoroacetyl-L-glutamic acid 1-ethyl ester-5-acid chloride (I) with diazomethane in ether gives 6-diazo-5-oxonorleucine ethyl ester (II),which can be hydrolyzed by treatment with ammonia or NaOH in ethanol water.2) The hydrogenation of gamma-benzyl ester of N-carboxy-L-glutamate anhydride (III) with H2 over Pd/C in ethyl acetate gives N-carboxy-L-glutamate anhydride (IV),which by reaction with refluxing SOCl2 yields L-4-[2-(chlorocarbonyl)ethyl]oxazolidine-2,5-dione (V).The reaction of (V) with diazomethane in ether affords L-4-(4-diazo-3-oxobutyl)oxazolidine-2,5-dione (VI),which is finally hydrolyzed with NaOH in water at room temperature.
参考文献标题:N-Trifluoroacetylamine acids.XI.Synthesis of 6-diazo-5-oxo-L-norleucine and 7-diazo-6-oxo-L-2-aminoheptylic acid
文献作者:Weygand,F.; et al.
参考来源:Chem Ber 1958,911037-40
合成路线:Compound can be prepared in two different ways:1) The reaction of N-trifluoroacetyl-L-glutamic acid 1-ethyl ester-5-acid chloride (I) with diazomethane in ether gives 6-diazo-5-oxonorleucine ethyl ester (II),which can be hydrolyzed by treatment with ammonia or NaOH in ethanol water.2) The hydrogenation of gamma-benzyl ester of N-carboxy-L-glutamate anhydride (III) with H2 over Pd/C in ethyl acetate gives N-carboxy-L-glutamate anhydride (IV),which by reaction with refluxing SOCl2 yields L-4-[2-(chlorocarbonyl)ethyl]oxazolidine-2,5-dione (V).The reaction of (V) with diazomethane in ether affords L-4-(4-diazo-3-oxobutyl)oxazolidine-2,5-dione (VI),which is finally hydrolyzed with NaOH in water at room temperature.
参考文献标题:DON
文献作者:Cabanillas,F.; Serradell,M.N.; Blancafort,P.; Casta馿r,J.
参考来源:Drugs Fut 1979,4(8),572