(S)-5-(N-methyl-tert-butoxycarbonylamino)-2,3,4,5-tetrahydro-1H-1-benzazepine | 294196-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: (S)-5-(N-methyl-tert-butoxycarbonylamino)-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: tert-butyl N-methyl-N-[(5S)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-yl]carbamate
• CAS: 294196-05-7
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: SBINBRKGNSEVSU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-(N-methyl-tert-butoxycarbonylamino)-2,3,4,5-tetrahydro-1H-1-benzazepine 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-5-methylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  Enantioselective Synthesis of the Metabolites of Vasopressin V2 Receptor Antagonist OPC-31260 via Lipase-Catalyzed Transesterification

  摘要：

  The optical isomers of 5-dimethylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-31260, 1) and its metabolites (2, 3, 4, 5 and 6) were enantioselectively synthesized. The chiral acetate 8b and alcohol 7a were prepared via the resolution of the racemic alcohol (+/-)-7 using the lipase-mediated transesterification in vinyl acetate. The compounds 8b and 7a were converted to the hydroxy metabolites (2a and 2b), the methylamine metabolites (3a and 3b), the dimethylamines (1a and 1b), and the amine metabolites (4a and 4b) in several steps while maintaining their absolute configurations. The 4,5-diol metabolites (5a, 5b, 6a and 6b) were synthesized from the key intermediates obtained by the lipase-catalyzed transesterification. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00388-4
• 作为产物：
  描述：

  (S)-5-(N-methyl-tert-butoxycarbonylamino)-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以78%的产率得到(S)-5-(N-methyl-tert-butoxycarbonylamino)-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  Enantioselective Synthesis of the Metabolites of Vasopressin V2 Receptor Antagonist OPC-31260 via Lipase-Catalyzed Transesterification

  摘要：

  The optical isomers of 5-dimethylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-31260, 1) and its metabolites (2, 3, 4, 5 and 6) were enantioselectively synthesized. The chiral acetate 8b and alcohol 7a were prepared via the resolution of the racemic alcohol (+/-)-7 using the lipase-mediated transesterification in vinyl acetate. The compounds 8b and 7a were converted to the hydroxy metabolites (2a and 2b), the methylamine metabolites (3a and 3b), the dimethylamines (1a and 1b), and the amine metabolites (4a and 4b) in several steps while maintaining their absolute configurations. The 4,5-diol metabolites (5a, 5b, 6a and 6b) were synthesized from the key intermediates obtained by the lipase-catalyzed transesterification. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00388-4

文献信息

• Enantioselective Synthesis of the Metabolites of Vasopressin V2 Receptor Antagonist OPC-31260 via Lipase-Catalyzed Transesterification
  作者：Jun Matsubara、Kazuyoshi Kitano、Kenji Otsubo、Yoshikazu Kawano、Tadaaki Ohtani、Masahiko Bando、Masaru Kido、Minoru Uchida、Fujio Tabusa

  DOI：10.1016/s0040-4020(00)00388-4

  日期：2000.6

  The optical isomers of 5-dimethylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine (OPC-31260, 1) and its metabolites (2, 3, 4, 5 and 6) were enantioselectively synthesized. The chiral acetate 8b and alcohol 7a were prepared via the resolution of the racemic alcohol (+/-)-7 using the lipase-mediated transesterification in vinyl acetate. The compounds 8b and 7a were converted to the hydroxy metabolites (2a and 2b), the methylamine metabolites (3a and 3b), the dimethylamines (1a and 1b), and the amine metabolites (4a and 4b) in several steps while maintaining their absolute configurations. The 4,5-diol metabolites (5a, 5b, 6a and 6b) were synthesized from the key intermediates obtained by the lipase-catalyzed transesterification. (C) 2000 Elsevier Science Ltd. All rights reserved.