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Iodixanol, DU-6807, 2-5410-3A, OptiPrep, Visipaque, Acupaque

碘克沙醇Chemical Name: 5,5'-[(2-Hydroxytrimethylene)bis(acetylimino)]bis[N,N/1-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide
CAS No. 92339-11-2
项目整合开发状态: Launched-1993
项目研究机构: Amersham Health (Originator), Daiichi Pharmaceutical (Licensee)
合成路线:The title compound is prepared by condensation of the acetamido isophthalamide (I) with epichlorohydrin (II) in 2-methoxyethanol.
📌 参考资料/链接:
参考文献标题:X-ray contrast agents
文献作者:Wille,K.; Hansen,P.-E.; Holtermann,H.(Amersham plc)
参考来源:EP 0108638; US 5349085

📄 详细内容


合成路线:In an improved method,the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II).Subsequent alkylation of (II) with 1-chloro-3-methoxy-2-propanol (III) yields regioselectively the N-alkylated acetamide (IV).The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线:In a different strategy,the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II).Subsequent condensation of (II) with epichlorohydrin (III) yields the dimeric adduct (IV).The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线:In an improved method,the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II).Subsequent alkylation of (II) with 2-chloroethanol (III) yields regioselectively the N-alkylated acetamide (IV).The borate groups of (IV) are finally removed upon quenching with diluted HCl.

参考文献标题:An N-alkylation
文献作者:Priebe,H.(Amersham plc)
参考来源:GB 2331098


合成路线:The title compound is prepared by condensation of the acetamido isophthalamide (I) with epichlorohydrin (II) in 2-methoxyethanol.

参考文献标题:Process for the production of iodinated organic X-ray contrast agents
文献作者:Cockbain,J.; Malthe-Soerenssen,D.; Schelver Hyni,A.C.; Aabye,A.; Bjoersvik,H.R.; Brekke,G.; Sjoegren,C.E.(Amersham plc)
参考来源:WO 9823296


合成路线:The title compound is prepared by condensation of the acetamido isophthalamide (I) with epichlorohydrin (II) in 2-methoxyethanol.

参考文献标题:Preparation of iodixanol
文献作者:Skailes,H.J.; Homestad,O.M.(Amersham plc)
参考来源:WO 0047549


合成路线:In an alternative method,the tetra-acid chloride (I) derived from O-acetyl-iodixanol is condensed with 3-amino-1,2-propanediol (II) under Schotten-Baumann conditions to afford amide (III).The acetate ester group of (III) is then removed by acidic hydrolysis to furnish the title compound.

参考文献标题:N-acylation reactions performed in aqueous reaction medium: Screening and optimising of a synthetic step of a process for iodixanol
文献作者:Bjoersvik,H.-R.; et al.
参考来源:Org Process Res Dev 2002,6(2),113


合成路线:In an improved method,the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II).Subsequent alkylation of (II) with 1-chloro-3-methoxy-2-propanol (III) yields regioselectively the N-alkylated acetamide (IV).The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线:In a different strategy,the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II).Subsequent condensation of (II) with epichlorohydrin (III) yields the dimeric adduct (IV).The borate groups of (IV) are finally removed upon quenching with diluted HCl.

合成路线:In an improved method,the acetamido isophthalamide (I) is treated with boric acid and KOH to form the cyclic diborate tripotassium salt (II).Subsequent alkylation of (II) with 2-chloroethanol (III) yields regioselectively the N-alkylated acetamide (IV).The borate groups of (IV) are finally removed upon quenching with diluted HCl.
参考文献标题:A selective process for N-alkylation in competition with O-alkylation: Boric acid,borax,and metaborate as a cheap and effective protecting group applicable for industrial-scale synthetic processes
文献作者:Bjoersvik,H.-R.; et al.
参考来源:Org Process Res Dev 2001,5(5),472


产品链接: CAS No. 92339-11-2››