2-oxo-1,3-dibenzylamino-cis-4,5-imidazolidinedicarboxylic acid anhydride

• 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-oxo-1,3-dibenzylamino-cis-4,5-imidazolidinedicarboxylic acid anhydride
• 英文别名: (3aS,6aR)-3a-amino-1,3-dibenzyl-6aH-furo[3,4-d]imidazole-2,4,6-trione
• 化学式: C₁₉H₁₇N₃O₄
• 分子量: 351.362
• InChiKey: MYMRYEFCPNAHFI-KXBFYZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  92.9
• 氢给体数：
  1
• 氢受体数：
  5

文献信息

• Process for preparing biotin
  申请人：F. Hoffmann-La Roche AG

  公开号：US20010020101A1

  公开（公告）日：2001-09-06

  The present invention is directed to a process for the production of 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid and of 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid anhydride, starting from meso-2,3-bis(benzylamino)succinic acid dialkali metal salt. The process involves reacting meso-2,3-bis(benzylamino)succinic acid dialkali metal salt with phenyl chloroformate in a monophasic solvent system consisting of an about 2:1 to 1:1 mixture of a water-miscible ether and an aqueous alkali metal hydroxide solution, at a temperature not exceeding about 40° C. The resulting 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid dialkali metal salt is converted, by acidification, into the desired 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid, which is then either isolated, or converted, by heating with acetic anhydride, in an aromatic hydrocarbon as the organic solvent, into the desired 2-oxo-1,3-dibenzyl-cis-4,5-imidazolidinedicarboxylic acid anhydride, which is in turn, isolated. Each product is an important intermediate in the multi-stage process for the manufacture of biotin (vitamin H).

  本发明涉及一种从中性2,3-双(苄氨基)琥珀酸二碱金属盐出发制备2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸和2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸酐的工艺。该工艺包括将中性2,3-双(苄氨基)琥珀酸二碱金属盐与苯基氯甲酸酯在单相溶剂体系中反应，所述单相溶剂体系由水溶性醚和含有碱金属氢氧化物的水溶液的约2:1至1:1混合物组成，反应温度不超过约40°C。生成的2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸二碱金属盐通过酸化转化为所需的2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸，然后可以将其分离或者通过与乙酸酐在芳香烃作为有机溶剂的条件下加热转化为所需的2-氧代-1,3-双苄基-顺式-4,5-咪唑烷二羧酸酐，然后将其分离。每种产品都是生产生物素（维生素H）的多阶段过程中的重要中间体。