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【结 构 式】 
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【分子编号】16008 【品名】(1S)-2-[3-[[(3-[[3-[[(2S)-2-(acetoxy)propanoyl]amino]-5-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl)-2,4,6-triiodobenzoyl]amino]-2-hydroxypropyl)amino]carbonyl]-5-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl)-2,4,6-triiodoanilino]-1-methyl-2-oxoethyl acetate 【CA登记号】 |
【 分 子 式 】C35H40I6N6O15 【 分 子 量 】1546.16086 【元素组成】C 27.19% H 2.61% I 49.25% N 5.44% O 15.52% |
合成路线1
该中间体在本合成路线中的序号：(III)The synthetic pathway is shown in Scheme 19316401a: Treatment of (S)-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarbonyldichloride (I) with 2-amino-1,3-propanediol in diglyme yields (S)-3-[(2-acetyloxy-1-oxopropyl)amino]-5-[[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl]-2,4,6-triiodobenzenecarbonylchloride (II). Compound (II) is treated with 1,3-diamino-2-propanol to give the dimeric compound [(S)-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide] (III). Hydrolysis of compound (III) and desalting of its aqueous solution gives a crude [S-(R*,R*)]-N,N''-(2-hydroxy-1,3-propanediyl)bis[N'-[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide, which is subsequently purified through a bed of adsorbent resin.
| 【1】 Heimann, G.; Kollenkirchen, U.; Miklautz, H.; Krause, W.; Physicochemical parameters of X-ray contrast media. Invest Radiol 1994, 29, 72-80. |
| 【2】 Renaa, T.; Jakobsen, T.; Contrast media research. An investment for the future. Acta Radiol 1987, Suppl. 370, 9-11. |
| 【3】 Luzzani, F.L.; Haen, C.; Iofratol. Drugs Fut 1995, 20, 11, 1120. |
| 【4】 Uggeri, F.; Brocchetta, M. (Bracco SpA); 1,3-Bis[3-(mono- or poly-hydroxy)acylamino-5-(mono- or poly-hydroxyalkyl)aminocarbonyl-2,4,6-triiodo-benzoyl-amino]-hydroxy-or hydroxyalkyl-propanes, their methods of preparation and X-ray contrast media containing them. EP 0557345; JP 1994504268; WO 9208691 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 23333 | 2-amino-1,3-propanediol; serinol | 534-03-2 | C3H9NO2 | 详情 | 详情 | |
| 47975 | 1,3-diamino-2-propanol | 616-29-5 | C3H10N2O | 详情 | 详情 | |
| (I) | 16006 | (1S)-2-[3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilino]-1-methyl-2-oxoethyl acetate | C13H8Cl2I3NO5 | 详情 | 详情 | |
| (II) | 16007 | (1S)-2-[3-(chlorocarbonyl)-5-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl)-2,4,6-triiodoanilino]-1-methyl-2-oxoethyl acetate | C16H16ClI3N2O7 | 详情 | 详情 | |
| (III) | 16008 | (1S)-2-[3-[[(3-[[3-[[(2S)-2-(acetoxy)propanoyl]amino]-5-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl)-2,4,6-triiodobenzoyl]amino]-2-hydroxypropyl)amino]carbonyl]-5-([[2-hydroxy-1-(hydroxymethyl)ethyl]amino]carbonyl)-2,4,6-triiodoanilino]-1-methyl-2-oxoethyl acetate | C35H40I6N6O15 | 详情 | 详情 |