γ-Cyano-α-L-benzyloxycarbonylamino-buttersaeure-ethylester | 864296-75-3

• 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: γ-Cyano-α-L-benzyloxycarbonylamino-buttersaeure-ethylester
• 英文别名: (S)-2-(benzyloxycarbonylamino)-4-cyanobutanoate；(2S)-2-(benzyloxycarbonyl-amino)-4-cyano-butyric acid ethyl ester；ethyl(2S)-2-(benzyloxycarbonyl-amino)-4-cyano-butyrate；ethyl (2S)-4-cyano-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 864296-75-3
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: ROVHPAPIBNTOFU-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  γ-Cyano-α-L-benzyloxycarbonylamino-buttersaeure-ethylester 在 sodium azide 、 三乙胺盐酸盐 、 盐酸 作用下， 以 甲苯 、 水 为溶剂， 反应 24.0h， 以79%的产率得到(2S)-2-(benzyloxycarbonyl-amino)-4-(1H-tetrazol-5-yl)-butyric acid ethyl ester
  参考文献：
  名称：

  [DE] NEUE CARBONSÄUREAMIDE ALS FAKTOR XA-INHIBITOREN
  [EN] NOVEL CARBOXAMIDES FOR USE AS XA INHIBITORS
  [FR] NOUVEAUX CARBOXAMIDES COMME INHIBITEURS DU FACTEUR XA

  摘要：

  The subject of the present invention is new substituted carboxylic acid amides of the general formula (I), in which A, B, and R1 to R5 are as defined in claim 1, their tautomers, their enantiomers, their diastereomers, their mixtures, and their salts, especially their physiologically acceptable salts with inorganic or organic acids or bases, which have valuable properties. The compounds have an antithrombotic effect and are Factor Xa inhibitors.

  公开号：

  WO2005082895A1
• 作为产物：
  描述：

  Z-Gln-OEt 在 吡啶 、 对甲苯磺酰氯 作用下， 生成 γ-Cyano-α-L-benzyloxycarbonylamino-buttersaeure-ethylester
  参考文献：
  名称：

  从 L-谷氨酰胺合成 L-脯氨酸

  摘要：

  1. 描述了从光学活性谷氨酰胺合成光学活性脯氨酸和鸟氨酸的新方法。2.羧基-L-谷氨酰胺酯与对甲苯磺酰氯、三氯氧磷或亚硫酰氯脱水生成γ-氰基-α-L-羧基苯甲氧基氨基丁酸酯。3. γ-氰基-α-L-羧基苯甲氧基氨基丁酸酯在水性溶剂体系中通过丝-钯催化剂加氢，主要生成L-脯氨酸。4、在阮内镍存在下，在非水溶剂中加氢得到L-鸟氨酸。

  DOI：

  10.1246/bcsj.36.25

文献信息

• New carboxylic acid amides, the preparation thereof and their use as medicaments
  申请人：Priepke Henning

  公开号：US20050203078A1

  公开（公告）日：2005-09-15

  The present invention relates to new substituted carboxylic acid amides of general formula wherein A, B and R 1 to R 5 are defined as in claim 1, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一般式的新取代羧酸酰胺 其中A、B和R1至R5如权利要求1中定义，其互变异构体、对映体、非对映异构体、它们的混合物及其盐，特别是其与无机或有机酸或碱形成的生理上可接受的盐，具有有价值的性质。
• A Novel Rearrangement of Cyclic Glutamine Derivatives: Ring Contraction in 3,6-Diamino-2,3,4,5-tetrahydropyridin-2-ones to Yield 5-Iminoproline Amides
  作者：Vladimir N. Belov、Viktor V. Sokolov、Boris D. Zlatopolskiy、Armin de Meijere

  DOI：10.1002/ejoc.201100404

  日期：2011.8

  A new rearrangement of the cyclic L-glutamine derivative(S)-6-carbamoylamino-3-(methylamino)-2,3,4,5-tetrahydropyridin-2-one (2) and its descarbamoyl analogue 10-H was found to yield enantiomerically pure 5-carbamoylimino-1-methyl-L-proline amide (12-CONH2) and its descarbamoyl analogue 12-H, respectively. Cyclic amidines 2 and 10-H were generated from the amide N2-ZGlnOEt 3 in seven and six steps

  发现环状 L-谷氨酰胺衍生物 (S)-6-carbamoylamino-3-(methylamino)-2,3,4,5-tetrahydropyridin-2-one (2) 及其去氨基甲酰基类似物 10-H 的新重排分别产生对映异构纯 5-carbamoylimino-1-methyl-L-proline 酰胺 (12-CONH2) 和它的 descarbamoyl 类似物 12-H。环脒 2 和 10-H 分别通过七步和六步从酰胺 N2-ZGlnOEt 3 产生。(S)-6-amino-3-[(N-benzyloxycarbonyl-N-methyl)amino]-2,3,4,5-tetrahydropyridin-2-one (8) 的脱保护直接导致 5-iminoproline 酰胺 12- H（通过 10-H 和双环邻脒 11-H）以 66% 的总产率从 3. 8 与 ZNCO（Z
• NEW CARBOXYLIC ACID AMIDES, THE PREPARATION THEREOF AND THEIR USE AS MEDICAMENTS
  申请人：PRIEPKE Henning

  公开号：US20080146539A1

  公开（公告）日：2008-06-19

  The present invention relates to new substituted carboxylic acid amides of general formula wherein A, B and R 1 to R 5 are defined as in claim 1 , the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一种新的取代羧酸酰胺，其一般式为其中A、B和R1至R5如权利要求1所定义，其互变异构体、对映异构体、顺反异构体、混合物及其与无机或有机酸或碱的生理上可接受的盐，具有有价值的性质。
• Carboxylic acid amides, the preparation thereof and their use as medicaments
  申请人：Boehringer Ingelheim International GmbH

  公开号：US07947700B2

  公开（公告）日：2011-05-24

  The present invention relates to new substituted carboxylic acid amides of general formula wherein A, B and R1 to R5 are defined as in claim 1, the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一种具有有价值性质的新取代羧酸酰胺，其一般式为其中A、B和R1至R5如权利要求1所定义，其互变异构体、对映异构体、顺反异构体、其混合物及其盐，特别是其与无机或有机酸或碱的生理上可接受的盐。
• CARBOXYLIC ACID AMIDES, THE PREPARATION THEREOF AND THEIR USE AS MEDICAMENTS
  申请人：PRIEPKE Henning

  公开号：US20130237522A1

  公开（公告）日：2013-09-12

  The present invention relates to new substituted carboxylic acid amides of general formula wherein A, B and R 1 to R 5 are defined as in claim 1 , the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及新的取代羧酸酰胺，其一般式为 A、B 和 R1 到 R5 如权利要求1所定义，其互变异构体、对映异构体、顺反异构体、混合物及其与无机或有机酸或碱的生理上可接受的盐，具有有价值的性质。