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【结 构 式】

【分子编号】31199

【品名】N(1),N(3)-bis(2,3-dihydroxypropyl)-5-hydroxy-2,4,6-triiodoisophthalamide

【CA登记号】

【 分 子 式 】C14H17I3N2O7

【 分 子 量 】706.01167

【元素组成】C 23.82% H 2.43% I 53.92% N 3.97% O 15.86%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

5-Hydroxy-1,3-benzenedicarboxylic acid dimethyl ester (I) is treated with 3-amino-1,2-propanediol to give the corresponding bisamide (II), which is then iodinated with iodine monochloride. The reaction of the triiodinated compound thus obtained (III) with sodium methoxide and chloroacetic acid ethyl ester yields N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[2-ethoxy-2-oxoethoxy]-1,3-benzenedicarboxamide (IV), which is treated with methylamine to give the 5-[2-(methylamino)-2-oxoethoxy] derivative (V). Iomeprol is obtained through a Smiles-type intramolecular rearrangement of (V) in aqueous alkaline medium.

1 Felder, E.; Pitre, D. (Bracco SpA); Derivs. of 2,4,6-triiodo-isophthalic acid, processes for their synthesis and x-ray contrasting materials containing these. EP 0026281; US 4352788 .
2 Davies, A.; Felder, E.; Tirone, P.; IOMEPROL < Rec INN; BAN; USAN >. Drugs Fut 1990, 15, 11, 1074.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 12979 3-Amino-1,2-propanediol;3-aminopropane-1,2-diol 616-30-8 C3H9NO2 详情 详情
(A) 16601 ethyl chloroacetate; ethyl 2-chloroacetate 105-39-5 C4H7ClO2 详情 详情
(I) 31197 dimethyl 5-hydroxyisophthalate 13036-02-7 C10H10O5 详情 详情
(II) 31198 N(1),N(3)-bis(2,3-dihydroxypropyl)-5-hydroxyisophthalamide C14H20N2O7 详情 详情
(III) 31199 N(1),N(3)-bis(2,3-dihydroxypropyl)-5-hydroxy-2,4,6-triiodoisophthalamide C14H17I3N2O7 详情 详情
(IV) 31200 ethyl 2-(3,5-bis[[(2,3-dihydroxypropyl)amino]carbonyl]-2,4,6-triiodophenoxy)acetate C18H23I3N2O9 详情 详情
(V) 31201 N(1),N(3)-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[2-(methylamino)-2-oxoethoxy]isophthalamide C17H22I3N3O8 详情 详情
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