1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid | 118783-83-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid
• 英文别名: (E)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid；3-(1-carboxycyclopentyl)-2-(2-methoxyethoxymethyl)-propanoic acid t-butyl ester；1-[2'-(tert-butoxycarbonyl)-3'-(2-methoxyethoxy)propyl]cyclopentane-1-carboxylic acid；1-[2-(2-methoxyethoxymethyl)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclopentane-1-carboxylic acid
• CAS: 118783-83-8
• 化学式: C₁₇H₃₀O₆
• 分子量: 330.422
• InChiKey: HYBVWCCIEBYQJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±20.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid 在 potassium tert-butylate 、 sodium hydroxide 作用下， 以 正己烷 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 20.0h， 生成 tert-butyl (S)-N-{1-[2-(tert-butyloxycarbonyl)-2-propenyl]-1-cyclopentylcarbonyl}-O4-tert-butyltyrosinate
  参考文献：
  名称：

  The Chemical Development and Scale-Up of Sampatrilat¹

  摘要：

  The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.

  DOI：

  10.1021/op020091f
• 作为产物：
  描述：

  tert-butyl 2-(2-methoxyethoxymethyl)acrylate 在 硫酸 、 potassium tert-butylate 、 双氧水 作用下， 以 水 、 乙腈 、 叔丁醇 为溶剂， 反应 66.0h， 生成 1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid
  参考文献：
  名称：

  2-乙酰环己酮氧化环缩合合成宝石-环戊基取代戊二酸酯

  摘要：

  摘要 已经从 2-乙酰环己酮和丙烯酸酯开发了一种两步法合成受差别保护的 gem-环戊基戊二酸酯。关键步骤涉及与过氧化氢的氧化缩环反应。该方法已用于制备用于制备四肽酶抑制剂坎多沙曲的中间体。

  DOI：

  10.1081/scc-120012979

文献信息

• Glutaramide diuretic agents
  申请人：Pfizer Inc.

  公开号：US05030654A1

  公开（公告）日：1991-07-09

  A series of novel spiro-substituted glutaramide derivatives have been prepared, including the pharmaceutically acceptable salts thereof and bioprecursors therefor, wherein the spiro-substituent completes a 5- or 6-membered carbocycyclic ring and is located at the carbon atom adjacent to the carbamoyl group. These particular compounds are inhibitors of the neutral endopeptidase E.C.3.4.24.11 enzyme and are therefore useful in therapy as diuretic agents for the treatment of hypertension, heart failure, renal insufficiency and other disorders. Methods for preparing these compounds from known starting materials are provided.

  已制备了一系列新颖的螺环取代谷氨酰胺衍生物，包括其药用可接受盐和生物前体，其中螺环取代基完成一个5-或6-成员碳环，并位于相邻于羰胺基团的碳原子上。这些特定化合物是中性内切肽酶E.C.3.4.24.11酶的抑制剂，因此在治疗高血压、心力衰竭、肾功能不全和其他疾病中作为利尿剂剂而有用。提供了从已知起始物质制备这些化合物的方法。
• [EN] CYCLOPENTYL-SUBSTITUTED GLUTARAMIDE DERIVATIVES AS INHIBITORS OF NEUTRAL ENDOPEPTIDASE<br/>[FR] DERIVES DE GLUTARAMIDE SUBSTITUES PAR DU CYCLOPENTYL UTILISES COMME INHIBITEURS DE L'ENDOPEPTIDASE NEUTRE
  申请人：PFIZER LTD

  公开号：WO2002002513A1

  公开（公告）日：2002-01-10

  The invention provides compounds of formula I wherein R1 is optionally substituted C¿1?-6alkyl, optionally substituted C3-7 cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl; n is 0, 1 or 2; and Y is -NR?18S(O)¿uR19 or a group shown below.

  该发明提供了公式I的化合物，其中R1是可选取代的C1-6烷基，可选取代的C3-7环烷基，可选取代的芳基或可选取代的杂环基；n为0，1或2；Y为-NR?18S(O)uR19或下图所示的基团。
• Preparation of glutaric acid derivatives
  申请人：Pfizer Inc.

  公开号：US05166406A1

  公开（公告）日：1992-11-24

  The invention provides a process for preparing a compound of the formula: ##STR1## or a base salt thereof, wherein R.sup.2 is hydrogen or C.sub.1 -C.sub.6 alkyl optionally substituted by up to 3 substituents each independently selected from the group consisting of C.sub.1 -C.sub.6 alkoxy and C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6 alkoxy)-; and R.sup.3 is C.sub.1 -C.sub.6 alkyl or benzyl, said benzyl group being optionally ring-substituted by up to 2 nitro or C.sub.1 -C.sub.4 alkoxy substituents comprising reacting a compound of the formula: ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl or C.sub.1 -C.sub.4 alkoxy; and R.sup.2 and R.sup.3 are as previously defined for a compound of the formula (I), with hydrogen peroxide or a source of peroxide ions: said process being optionally followed by conversion of the compound of the formula (I) to a base salt thereof. The present invention also relates to novel compounds of the formula (II).

  本发明提供了一种制备式为：##STR1##或其碱盐的化合物的过程，其中R.sup.2是氢或C.sub.1-C.sub.6烷基，可选地被选自C.sub.1-C.sub.6烷氧基和C.sub.1-C.sub.6烷氧基（C.sub.1-C.sub.6烷氧基）的3个取代基中的每个独立选择的取代基取代；R.sup.3是C.sub.1-C.sub.6烷基或苄基，所述的苄基可选地被选自最多2个硝基或C.sub.1-C.sub.4烷氧基取代，包括将式为：##STR2##其中R.sup.1是C.sub.1-C.sub.4烷基，苯基或苄基或C.sub.1-C.sub.4烷氧基; R.sup.2和R.sup.3如前所述对于式(I)的化合物，与过氧化氢或过氧化物离子的来源反应：该过程随后可选择将式(I)的化合物转化为其碱盐。本发明还涉及式(I)的新化合物。
• Cyclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase
  申请人：——

  公开号：US20020052370A1

  公开（公告）日：2002-05-02

  The invention provides compounds of formula I wherein R 1 is optionally substituted C 1-6 alkyl, optionally substituted C 3-7 cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl; n is 0, 1 or 2; and Y is —NR 18 S(O) u R 19 or a group shown below. 1

  本发明提供了式I的化合物，其中R1是可选取代的C1-6烷基，可选取代的C3-7环烷基，可选取代的芳基或可选取代的杂环基；n为0、1或2；Y为—NR18S(O)uR19或下图所示的基团1。
• Hydrogenation
  申请人：Pfizer Limited

  公开号：EP0644176A1

  公开（公告）日：1995-03-22

  Compounds of formula (I) or (Ia): where R is 5-indanyl or a carboxylic acid protecting group, or an amine salt thereof, are prepared by hydrogenating an (E)-allylic ether of formula (II) or (IIa): in the presence of a stereoselective rhodium or ruthenium biphosphine catalyst and a protic solvent.

  式 (I) 或 (Ia) 的化合物： 式（II）或（IIa）的(E)-烯丙基醚通过氢化制备，其中 R 为 5-茚基或羧酸保护基团或其胺盐： 在立体选择性铑或钌双膦催化剂和质子溶剂存在下进行氢化制备。