Z-4105

4-[(3-甲基-1,2-恶唑-5-羰基)氨基]丁酸Chemical Name: N-(3-Carboxypropyl)-3-methylisoxazole-5-carboxamide; 4-(3-Methylisoxazol-5-ylcarboxamido)butyric acid
CAS No. 119737-52-9
项目整合开发状态: Preclinical
项目研究机构: Zambon (Originator)
合成路线:Z-4105 was prepared according to the reaction sequence as follows:The isoxazole intermediate (III) was obtained by one-pot 1,3-dipolar cycloaddition between acetonitrile oxide,in situ generated from chlorooxime (II),and propargyl alcohol.The oxidation of compound (III) with potassium permanganate gave the acid (IV),which was subsequently converted into the acid chloride (V) by Burdett's method.Finally,Z-4105 was synthesized from (V) and gamma-aminobutyric acid by means of Schotten-Baumann procedure.
📌 参考资料/链接:
参考文献标题:Isoxazoles with nootropic activity
文献作者:Carenzi,A.; Chiarino,D.; Della Bella,D.; Napoletano,M.; Sala,A.(Zambon Group SpA)
参考来源:AU 8817869; EP 0317588; JP 1990500365; US 4985428; WO 8809330

📄 详细内容


合成路线:Z-4105 was prepared according to the reaction sequence as follows:The isoxazole intermediate (III) was obtained by one-pot 1,3-dipolar cycloaddition between acetonitrile oxide,in situ generated from chlorooxime (II),and propargyl alcohol.The oxidation of compound (III) with potassium permanganate gave the acid (IV),which was subsequently converted into the acid chloride (V) by Burdett's method.Finally,Z-4105 was synthesized from (V) and gamma-aminobutyric acid by means of Schotten-Baumann procedure.

参考文献标题:Z-4105
文献作者:Fusi,R.; Luperi,L.; Napoletano,M.; Ricciardi,S.; Masotto,C.
参考来源:Drugs Fut 1995,20(6),584


合成路线:Z-4105 was prepared according to the reaction sequence as follows:The isoxazole intermediate (III) was obtained by one-pot 1,3-dipolar cycloaddition between acetonitrile oxide,in situ generated from chlorooxime (II),and propargyl alcohol.The oxidation of compound (III) with potassium permanganate gave the acid (IV),which was subsequently converted into the acid chloride (V) by Burdett's method.Finally,Z-4105 was synthesized from (V) and gamma-aminobutyric acid by means of Schotten-Baumann procedure.

参考文献标题:Aliphatic chloro oximes and their application in the synthesis of isoxazole and beta-furanone systems
文献作者:Casnati,G.; Ricca,A.
参考来源:Tetrahedron Lett 1967,4327-30


合成路线:Z-4105 was prepared according to the reaction sequence as follows:The isoxazole intermediate (III) was obtained by one-pot 1,3-dipolar cycloaddition between acetonitrile oxide,in situ generated from chlorooxime (II),and propargyl alcohol.The oxidation of compound (III) with potassium permanganate gave the acid (IV),which was subsequently converted into the acid chloride (V) by Burdett's method.Finally,Z-4105 was synthesized from (V) and gamma-aminobutyric acid by means of Schotten-Baumann procedure.
参考文献标题:An improved acid chloride preparation via phase transfer catalysis
文献作者:Burdett,K.A.
参考来源:Synthesis 1991,441-2


产品链接: CAS No. 119737-52-9››