戊-O-乙酰基碘帕醇 | 289890-55-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 戊-O-乙酰基碘帕醇
• 英文名称: (S)-N,N'-bis[2-ethanoyloxy-1-[(ethanoyloxy)methyl]ethaneyl]-5-[(2-ethanoyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide
• 英文别名: (S)-N,N'-bis[2-ethanoyloxy-1-[(ethanoyloxy)methyl]ethyl]-5-[(2-ethanoyloxy-1-oxopropaneyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide；(S)-N,N'-Bis[2-acetyloxy-1-[(acetyloxy)methyl]ethyl]-5-[(2-acetyloxyl-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide；(S)-N,N'-Bis[2-acetyloxy-1-[(acetyloxy)methyl]ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide；(S)-N,N'-Bis[2-acetyloxy-1-[(acetyloxy)methyl]ethyl]-5-[(2-acetyloxyl-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide；(S)-N,N'-bis[2-acetyloxyl-[(acetyloxy)methyl]ethyl]-5-[(2-acetyloxyl-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide；(S)-((5-(2-acetoxypropanamido)-2,4,6-triiodoisophthaloyl)bis(azanediyl))-bis-(propane-2,1,3-triyl) tetraacetate；Pentaacetyliopamidol；[3-acetyloxy-2-[[3-[[(2S)-2-acetyloxypropanoyl]amino]-5-(1,3-diacetyloxypropan-2-ylcarbamoyl)-2,4,6-triiodobenzoyl]amino]propyl] acetate
• CAS: 289890-55-7
• 化学式: C₂₇H₃₂I₃N₃O₁₃
• 分子量: 987.277
• InChiKey: HTWGNAGGXTUGOV-NSHDSACASA-N

物化性质

• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  219
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  戊-O-乙酰基碘帕醇 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以93 %的产率得到碘帕醇
  参考文献：
  名称：

  KR20220139775A

  摘要：

  公开号：
• 作为产物：
  描述：

  5-氨基-2,4,6-三碘异酞酰氯 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 22.0h， 生成 戊-O-乙酰基碘帕醇
  参考文献：
  名称：

  KR20220139775A

  摘要：

  公开号：

文献信息

• Process for the preparation of iopamidol and the new intermediated therein
  申请人：——

  公开号：US20040082812A1

  公开（公告）日：2004-04-29

  A process for the preparation of (S)-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxo-propyl)amino]-2,4,6-triiodo-1,3-benzendicarboxamide (iopamidol) starling from 5-amino-N,N′-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (II) which process comprises a) reacting the compound of formula (II) with a suitable protecting agent, to give a compound of formula (III) wherein R is a group of formula A or B wherein R 1 is a hydrogen atom, a C 1 ÷C 4 straight or branched alkoxy group, R 2 is hydrogen, a C 1 ÷C 4 straight or branched alkoxy group and R 3 ?is a C 1 ÷C 4 straight or branched alkyl group, a trifuoromethyl or a trichloromethyl group; b) acylating the amino group in position 5 of the intermediate compound of formula (III), by reaction with a (S)-2-(acetyloxy)propanoyl chloride to give a compound of formula (IV) wherein R is as defined above; and c) removing all the acyl groups present in the compound of formula (IV) under basic conditions, with prior cleavage of the cyclic protections of the hydroxy groups in the carboxamido substituents under acidic conditions, when R is a group of formula A carboxamido hydroxy groups under acidic conditions. The invention also refers to the new intermediates of formula (III) and (IV) wherein —R is a group A.

  一种制备(S)-N,N′-双[2-羟基-1-(羟甲基)乙基]-5-[(2-羟基-1-氧代-丙基)氨基]-2,4,6-三碘-1,3-苯二甲酰胺（iopamidol）的过程，从5-氨基-N,N′-双[2-羟基-1-(羟甲基)乙基]-2,4,6-三碘-1,3-苯二甲酰胺（II）开始，该过程包括a）将式（II）的化合物与适当的保护剂反应，以给出式（III）的化合物，其中R是式A或B的基团，其中R1是氢原子，C1-C4直链或支链烷氧基，R2是氢，C1-C4直链或支链烷氧基，R3是C1-C4直链或支链烷基，三氟甲基或三氯甲基基团；b）通过与(S)-2-(乙酰氧)丙酰氯反应，酰化式（III）中位置5的氨基，以给出式（IV）的化合物，其中R如上所定义；和c）在碱性条件下去除化合物中存在的所有酰基，在酸性条件下先裂解羧酰胺取代基的羟基环保护，当R是式A羧酰胺基团时，在酸性条件下去除羟基环保护。该发明还涉及式（III）和（IV）的新中间体，其中-R是A基团。
• PROCESS FOR THE PREPARATION OF IOPAMIDOL
  申请人：Bracco Imaging SPA

  公开号：EP2975021A1

  公开（公告）日：2016-01-20

  A process for the preparation of (S)-N,N'-bis[2-hydroxy-1 (hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide (iopamidol) starting from 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (II) which process comprises a) reacting the compound of formula (II) with a suitable protecting agent, to give a compound of formula (III) wherein -R is a group of formula A or B wherein R1 is a hydrogen atom, a C1-C4 straight or branched alkyl group or a C1-C4 straight or branched alkoxy group, R2 is hydrogen, a C1-C4 straight or branched alkyl group or a C1-C4 straight or branched alkoxy group and R3 is a C1-C4 straight or branched alkyl group, a trifluoromethyl or a trichloromethyl group; b) acylating the amino group in position 5 of the intermediate compound of formula (III), by reaction with a (S)-2-(acetyloxy)propanoyl chloride to give a compound of formula (IV) wherein R is defined above; and c) removing all the acyl groups present in the compound of formula (IV) under basic conditions, with prior cleavage of the cyclic protections of the hydroxy groups in the carboxamido substituents under acidic conditions, when R is a group of formula A carboxamido hydroxy groups under acidic conditions.

  一种以 5-氨基-N,N'-双[2-羟基-1-(羟甲基)乙基]-5-[(2-羟基-1-氧代丙基)氨基]-2,4,6-三碘-1,3-苯二甲酰胺 (II) 为起始原料制备 (S)-N,N'- 双[2-羟基-1-(羟甲基)乙基]-5-[(2-羟基-1-氧代丙基)氨基]-2,4,6-三碘-1,3-苯二甲酰胺（碘帕醇）的方法 该工艺包括 a) 将式（II）化合物与合适的保护剂反应，得到式（III）化合物 其中 -R 是式 A 或 B 的基团 其中 R1 是氢原子、C1-C4 直链或支链烷基或 C1-C4 直链或支链烷氧基，R2 是氢、C1-C4 直链或支链烷基或 C1-C4 直链或支链烷氧基，R3 是 C1-C4 直链或支链烷基、三氟甲基或三氯甲基； b) 通过与(S)-2-(乙酰氧基)丙酰氯反应，使式(III)中间体化合物 5 位上的氨基酰化 反应，得到式（IV）化合物 其中 R 如上定义；以及 c) 当 R 为式 A 羧酰胺基羟基时，在碱性条件下除去式（IV）化合物中存在的所有酰基，并在酸性条件下先裂解羧酰胺基取代基中羟基的环保护层。
• A PROCESS FOR THE PREPARATION OF IOPAMIDOL
  申请人：BRACCO IMAGING S.p.A.

  公开号：EP1353899B1

  公开（公告）日：2016-01-20
• A PROCESS FOR THE PREPARATION OF IOPAMIDOL AND THE NEW INTERMEDIATES THEREIN
  申请人：Bracco Imaging S.p.A.

  公开号：EP1353899A1

  公开（公告）日：2003-10-22
• Process for the Preparation of Iopamidol
  申请人：Lorenzini A. Richard

  公开号：US20070078281A1

  公开（公告）日：2007-04-05

  The present invention discloses a process for the preparation of pure non-ionic contrast agents. The invention also includes a method for purifying the non-ionic contrast agents.