methyl (2R)-2-[[2-(tert-butoxycarbonylamino)acetyl]amino]-3-cyclohexylpropanoate | 917577-70-9

• 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: methyl (2R)-2-[[2-(tert-butoxycarbonylamino)acetyl]amino]-3-cyclohexylpropanoate
• 英文别名: methyl N-(tert-butoxycarbonyl)glycyl-3-cyclohexyl-D-alaninate；methyl (2R)-3-cyclohexyl-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoate
• CAS: 917577-70-9
• 化学式: C₁₇H₃₀N₂O₅
• 分子量: 342.436
• InChiKey: AOQDQFJMUAUMSG-CYBMUJFWSA-N

物化性质

• 沸点：
  496.9±25.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2R)-2-[[2-(tert-butoxycarbonylamino)acetyl]amino]-3-cyclohexylpropanoate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 N-(tert-butoxycarbonyl)glycyl-3-cyclohexyl-D-alanine
  参考文献：
  名称：

  Selection and Development of a Route for Cholesterol Absorption Inhibitor AZD4121

  摘要：

  The development of a synthetic route to the cholesterol absorption inhibitor AZD4121 is presented. Key steps are a highly enantioselective CBS reduction, a stereospecific Staudinger reaction, an amine/lithium chloride mediated ester hydrolysis, and a resolution of a 50:50 diastereomeric mixture by recrystallization. The synthesis was accomplished in 10 linear steps, and the overall yield, when compared with the lead optimization (LO) route, was improved from 1% to 20%. All purifications of intermediates through preparative HPLC or silica gel chromatography were avoided. This was possible since many of the intermediates along the route could be used as such in the next step until an intermediate with suitable crystalline properties could be identified and purified through crystallization.

  DOI：

  10.1021/op200314z
• 作为产物：
  描述：

  BOC-甘氨酸 、 D-环己基丙氨酸甲酯盐酸盐 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl (2R)-2-[[2-(tert-butoxycarbonylamino)acetyl]amino]-3-cyclohexylpropanoate
  参考文献：
  名称：

  WO2006/137793

  摘要：

  公开号：

文献信息

• New 2-Azetidinone Derivatives As Cholesterol Absorption Inhibitors For The Treatment Of Hyperlipidaemic Conditions
  申请人：Dahlstrom Mikael

  公开号：US20100048530A1

  公开（公告）日：2010-02-25

  The invention relates to 2-azetidinone derivatives of formula (I), including pharmaceutically acceptable salts, solvates and prodrugs thereof. The compounds inhibit cholesterol absorption and are useful in the treatment of hyperlipidaemic conditions. The invention also relates to processes for their manufacture and to pharmaceutical compositions containing them.

  该发明涉及公式（I）的2-氮杂环己酮衍生物，包括其药学上可接受的盐、溶剂和前药。这些化合物抑制胆固醇吸收，可用于治疗高脂血症状况。该发明还涉及制造它们的过程以及包含它们的药物组合物。
• New 2-Azetidinone Derivatives Useful In The Treatment Of Hyperlipidaemic Conditions
  申请人：Dahlstrom Mikael

  公开号：US20100048529A1

  公开（公告）日：2010-02-25

  The invention relates to compounds of formula (I) and pharmaceutically acceptable salts, solvates, and prodrugs thereof, and to their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia. The invention also relates to processes for their manufacture and pharmaceutical compositions containing them.

  本发明涉及公式(I)化合物及其药学上可接受的盐、溶剂化物和前药，以及它们作为胆固醇吸收抑制剂治疗高脂血症的用途。本发明还涉及它们的制造过程和含有它们的制药组合物。
• WO2006/137792
  申请人：——

  公开号：——

  公开（公告）日：——
• NEW 2-AZETIDINONE DERIVATIVES USEFUL IN THE TREATMENT OF HYPERLIPIDAEMIC CONDITIONS
  申请人：AstraZeneca AB

  公开号：EP1896457A1

  公开（公告）日：2008-03-12
• [EN] NEW 2-AZETIDINONE DERIVATIVES USEFUL IN THE TREATMENT OF HYPERLIPIDAEMIC CONDITIONS<br/>[FR] NOUVEAUX DÉRIVÉS DE 2-AZÉTIDINONE ET LEUR EMPLOI DANS LE TRAITEMENT DES ÉTATS PATHOLOGIQUES HYPERLIPÉMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2006137792A1

  公开（公告）日：2006-12-28

  [EN] The invention relates to compounds of formula (I) and pharmaceutically acceptable salts, solvates, and prodrugs thereof, and to their use as cholesterol absorption inhibitors for the treatment of hyperlipidaemia. The invention also relates to processes for their manufacture and pharmaceutical compositions containing them.
  [FR] La présente invention concerne des composés de formule (I) ainsi que les sels, solvates et prodrogues de qualité pharmaceutique desdits composés, et leur emploi en tant qu'inhibiteurs d'absorption de cholestérol pour le traitement d'hyperlipémies. La présente invention concerne également des procédés de fabrication desdits composés, ainsi que les préparations pharmaceutiques les contenant.