2,2',2''-(10-(1-Hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid | 138884-14-7

• 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
• 英文名称: 2,2',2''-(10-(1-Hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
• 英文别名: 2-[4,10-bis(carboxymethyl)-7-(1-hydroxypropan-2-yl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
• CAS: 138884-14-7
• 化学式: C₁₇H₃₂N₄O₇
• 分子量: 404.464
• InChiKey: VCXYHOKPOHBAJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Tribenzyl 10-<1-(Ethoxycarbonyl)ethyl>-1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 在 palladium on activated charcoal sodium hydroxide 、 锂硼氢 、 9-OMe-BBN 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 37.0h， 生成 2,2',2''-(10-(1-Hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid
  参考文献：
  名称：

  Synthesis of gadolinium (±)-10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate via tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate

  摘要：

  The synthesis of monogadolinium 10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate 12 has been achieved through a multistep sequence. The key step in the synthesis was the reaction of the previously unknown tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 6 with ethyl 2-(trifluoromethylsulphonyloxy)propionate 4 to give 7. Reduction of 7 with LiBH4/9-OMe-BBN, followed by hydrogenolysis of the protecting groups (Z groups) yielded 2-(1,4,7,10-tetraazacyclododec-1-yl)propanol 10. The monosubstituted macrocycle 10 was alkylated with bromoacetic acid and then complexed with gadolinium oxide to yield the title compound.

  DOI：

  10.1039/p19910003329

文献信息

• NOVEL PROCESS FOR THE PREPARATION OF MACROCYCLIC CHELANT 2,2',2''-(10-(2-HYDROXYPROPYL)-1,4,7,10-TETRA AZACYCLODODECANE-1,4,7-TRIYL) TRIACETIC ACID AND IT'S COMPLEXES WITH PARAMAGNETIC METAL IONS
  申请人：BIOPHORE INDIA PHARMACEUTICALS PVT. LTD

  公开号：US20210380542A1

  公开（公告）日：2021-12-09

  The present invention relates to an improved process for the preparation of macrocyclic chelant 2,2′,2″-(10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid of formula (1). The present invention further relates to the process for the preparation of metal complexes of macrocyclic chelant 2,2′,2″-(10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid of formula (1) with purity greater than 99.0% by HPLC. The present invention also relates to an improved process for the preparation of gadolinium complex of formula (1a) with macrocyclic chelant 2,2′,2″-(10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid of formula (1). The present invention further relates to a novel process for the preparation of calcium complex of formula (1b) with macrocyclic chelant 2,2′,2″-(10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl) triacetic acid of formula (1).
• Synthesis of gadolinium (±)-10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate via tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate
  作者：J. Siva Prasad、Frank J. Okuniewicz、Edward J. Delaney、Douglas D. Dischino

  DOI：10.1039/p19910003329

  日期：——

  The synthesis of monogadolinium 10-(1-hydroxypropan-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyltriacetate 12 has been achieved through a multistep sequence. The key step in the synthesis was the reaction of the previously unknown tribenzyl 1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 6 with ethyl 2-(trifluoromethylsulphonyloxy)propionate 4 to give 7. Reduction of 7 with LiBH4/9-OMe-BBN, followed by hydrogenolysis of the protecting groups (Z groups) yielded 2-(1,4,7,10-tetraazacyclododec-1-yl)propanol 10. The monosubstituted macrocycle 10 was alkylated with bromoacetic acid and then complexed with gadolinium oxide to yield the title compound.