(2S,3'R)-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenyl-butyric acid ethyl ester | 86499-39-0

• 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: (2S,3'R)-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenyl-butyric acid ethyl ester
• 英文别名: (R)-ethyl2-((S)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutanoate；ethyl (2S)-2-[[(3R)-2-oxo-1,3,4,5-tetrahydro-1-benzazepin-3-yl]amino]-4-phenylbutanoate
• CAS: 86499-39-0
• 化学式: C₂₂H₂₆N₂O₃
• 分子量: 366.46
• InChiKey: AGSGQWMQZLSVCI-UXHICEINSA-N

物化性质

• 沸点：
  573.6±50.0 °C(Predicted)
• 密度：
  1.17

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻硝基苯乙酮 在 palladium on activated charcoal 盐酸 、 baker's yeast 、 氢气 、 sodium ethanolate 、 alpha-氯乙酰苯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 水 为溶剂， 反应 102.0h， 生成 (2S,3'R)-2-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenyl-butyric acid ethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of ACE inhibitor-Benazepril HCl via a bioreductive reaction

  摘要：

  An enantioselective synthesis of the potent angiotensin converting enzyme (ACE) inhibitor (2S, 3'S)-2-(1-carboxymethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-4-phenylbutyric acid ethyl ester hydrochloride, Benazepril HCl 4, has been achieved through an asymmetric reduction of 4-(2-nitrophenyl)-2,4-dioxobutyric acid ethyl ester 6b employing baker's yeast as the reductive catalyst. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00453-1

文献信息

• Kinetic resolution of a intermediate useful in the production of benazepril and analogues thereof
  申请人：ScinoPharm Taiwan, Ltd.

  公开号：US20030055245A1

  公开（公告）日：2003-03-20

  The present invention provides an efficient synthetic process for making benazepril and analogues thereof by having an intermediate compound undergo epimerization and kinetic resolution.

  本发明提供了一种高效的合成过程，用于通过使中间化合物经历对映异构化和动力学分离来制备贝那普利及其类似物。
• KINETIC RESOLUTION OF A INTERMEDIATE USEFUL IN THE PRODUCTION OF BENAZEPRIL AND ANALOGUES THEREOF
  申请人：Scinopharm Taiwan, Ltd.

  公开号：EP1430031A2

  公开（公告）日：2004-06-23
• EP1430031A4
  申请人：——

  公开号：EP1430031A4

  公开（公告）日：2004-10-13
• [EN] PROCESS FOR PREPARATION OF 3-[(1'-(ALKOXYCARBONYL)-3'-PHENYLPROPYL)AMINO]-2-OXO-[1]-BENZAZEPINE AND ITS DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE 3-[(1'-(ALKOXYCARBONYL)-3'-PHENYLPROPYL)AMINO]-2-OXO-[1]-BENZAZEPINE ET DE SES DERIVES
  申请人：SCINOPHARM SINGAPORE PTE LTD

  公开号：WO2001079176A1

  公开（公告）日：2001-10-25

  The present invention relates to a process for the preparation of 3-[(1'-(alkoxycarbonyl)-3'-phenylpropyl)amino]-2-oxo-[1]-benzazepine, whose derivatives are angiotensin-converting enzyme (ACE) inhibitors useful in the treatment of hypertension, chronic heart failure and progressive chronic renal insufficiency. By using a non-natural amino acid ester, L-homophenylalanine alkyl ester, as a key starting material in the condensation with a 3-halo-2,3,4, 5-tetrahydro-1H-1-benzazepine-2-one which can be obtained easily in large quantities, the processes of the present invention can avoid racemization and require fewer steps in the operational procedures and are more practical and economical than conventional processes.
• [EN] KINETIC RESOLUTION OF A INTERMEDIATE USEFUL IN THE PRODUCTION OF BENAZEPRIL AND ANALOGUES THEREOF<br/>[FR] RESOLUTION CINETIQUE D'UN PRODUIT INTERMEDIAIRE UTILISE DANS LA PRODUCTION DE BENAZEPRIL ET D'ANALOGUES DE BENAZEPRIL
  申请人：SCINOPHARM TAIWAN LTD

  公开号：WO2003003972A2

  公开（公告）日：2003-01-16

  The present invention provides an efficient synthetic process for making benazepril and analogues thereof by having an intermediate compound undergo epimerization and kinetic resolution.