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【结 构 式】 
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【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% |
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 |