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Apomine, SR-45023A, SR-9223i, SK&F-99085

4-[2,2-二[二(丙-2-基氧基)磷酰]乙基]-2,6-二叔丁基苯酚Chemical Name: 2-(3,5-Di-tert-butyl-4-hydroxyphenyl)ethylidene-1,1-diphosphonic acid tetraisopropyl ester
CAS No. 126411-13-0
项目整合开发状态: Phase II
项目研究机构: Ilex Oncology (Originator)
合成路线:The title compound was prepared by several related methods.The sodium salt generated from tetraisopropyl methylenediphosphonate (I) and NaH was alkylated with 3,5-di-t-butyl-4-hydroxybenzyl chloride (II) in refluxing THF to afford the target arylethyl diphosphonate
📌 参考资料/链接:
参考文献标题:Phenol substd.gem-diphosphonate derivs.,process for their preparation and pharmaceutical compsns.containing them
文献作者:Nguyen,L.; Niesor,E.; Phan,H.; Maechler,P.; Bentzen,C.(Ilex Oncology Research-Europe SA)
参考来源:CH 675422; EP 0339237; JP 1990022285; US 5043330; US 5128331

📄 详细内容


合成路线:The title compound was prepared by several related methods.The sodium salt generated from tetraisopropyl methylenediphosphonate (I) and NaH was alkylated with 3,5-di-t-butyl-4-hydroxybenzyl chloride (II) in refluxing THF to afford the target arylethyl diphosphonate

合成路线:Alternatively,tetraisopropyl methylenediphosphonate (I) was alkylated with the benzyl alcohol (III) or with the dimethyl benzylamine (IV) in the presence of strong bases such as NaH or NaO-t-Bu

合成路线:In a related procedure,the dimethyl benzylamine (IV) was quaternized with iodomethane,and the resultant ammonium salt (V) was then condensed with the sodium salt of diphosphonate (I) (1).Other reported alkylating reagents included the bis-benzyl methyl amine (VII),prepared by Mannich reaction of methylamine with 2,6-di-t-butylphenol (VI) and formaldehyde,and the tris-benzyl amine (VIII),prepared by alkylation of ammonia with the benzyl chloride (II)

合成路线:In a further method,condensation of benzyl alcohol (III) with methanol in the presence of a catalytic amount of HCl afforded the corresponding methyl ether (IX),which was then reacted with diphosphonate (I) in the presence of NaH to furnish the target arylethyl diphosphonate (1).Optionally,diphosphonate (I) was condensed with the benzyl acetate ester (X),prepared from benzyl chloride (II) and potassium acetate in acetone
参考文献标题:A process for the preparation of diphosphonate derivs.
文献作者:Grinter,T.J.; Harris,M.A.; Hayler,J.D.; Negus,A.(Ilex Oncology Research-Europe SA)
参考来源:WO 9731004


产品链接: CAS No. 126411-13-0››