trans-4-tert-butylsulfinamidocyclohexanecarboxylic acid ethyl ester

• 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: trans-4-tert-butylsulfinamidocyclohexanecarboxylic acid ethyl ester
• 化学式: C₁₃H₂₅NO₃S
• 分子量: 275.412
• InChiKey: FUINGXVTZXYNLM-SIJBOIKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-4-tert-butylsulfinamidocyclohexanecarboxylic acid ethyl ester 在 吡啶 、 氯化亚砜 、 sodium tungstate (VI) dihydrate 、 硫酸 、 水 、 双氧水 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 3.0h， 生成 4-(tert-butylsulfonylamino)-N-[5-(trifluoromethyl)pyridin-2-yl]cyclohexane-1-carboxamide
  参考文献：
  名称：

  Development of an Optimized Synthetic and Purification Process of S-2367 (Velneperit), a Novel Neuropeptide Y (NPY) Y5 Receptor Antagonist

  摘要：

  We developed a simple synthetic route to S-2367 (Velneperit) (1) using trans-1-ethoxycarbonyl-4-aminocyclohexane hydrochloride salt (12) as a starting material. The key step was Na2WO4/H2O2 oxidation, and we found that it was accelerated in weakly basic conditions. The finding was useful to control one of the critical impurities: 14 in 10. The new process was more efficient than the early process from the viewpoint of the number of reactions, yield, throughput, and EHS (environment, health, and safety) but a quality deviation occurred in the pilot manufacturing: 10 content in 1 was over the upper limit. The cause was presumed to be hydrolysis of 1 during the recrystallization step. After finding it, we developed two reliable purification processes. The first was slurry washing including clever polymorphic control using only acetone and water. The second was salt formation of 10 and rational building of the recrystallization procedure based on solubility to improve removal rate.

  DOI：

  10.1021/acs.oprd.5b00023
• 作为产物：
  描述：

  叔丁基亚磺酰氯 、 trans-ethyl 4-aminocyclohexanecarboxylate hydrochloride 在 水 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.08h， 以94.6%的产率得到trans-4-tert-butylsulfinamidocyclohexanecarboxylic acid ethyl ester
  参考文献：
  名称：

  WO2006/106800

  摘要：

  公开号：

文献信息

• 一种反式4-(叔丁氧羰氨基)环己烷羧酸及其中间体的制备方法
  申请人：重庆医药高等专科学校

  公开号：CN113402428B

  公开（公告）日：2023-03-03

  本发明提供了一种反式4‑(叔丁氧羰氨基)环己烷羧酸及其中间体的制备方法，其特征在于包括如下制备步骤：以4‑氧代环己烷羧酸酯和手性配体试剂叔丁基亚磺酰胺为原料，在路易斯酸催化下还原胺化得到反式‑4‑叔丁基亚磺酰胺环己烷羧酸酯，本发明采用手性配体试剂叔丁基亚磺酰胺与4‑氧代环己烷羧酸酯缩合得到的中间体，使其还原反应具有高度立体选择性，反式产物的比例大于95％，同时叔丁基亚磺酰基团在碱性条件下稳定而在酸性条件下易离去，反应条件温和，操作简便，收率高，易于工业化生产。
• METHOD FOR PRODUCING SALT OF 4-SULFINYLAMINO-1-CYCLOHEXANECARBOXYLIC ACID
  申请人：Omura Sohei

  公开号：US20100076081A1

  公开（公告）日：2010-03-25

  Disclosed is a salt of trans-4-sulfinylamino-1-cyclohexanecarboxylic acid. Also disclosed is a method for producing a salt of trans-4-sulfinylamino-1-cyclohexanecarboxylic acid.

  本发明公开了一种trans-4-亚磺酰基氨基-1-环己烷羧酸的盐。本发明还公开了一种制备trans-4-亚磺酰基氨基-1-环己烷羧酸盐的方法。
• WO2006/106800
  申请人：——

  公开号：——

  公开（公告）日：——
• Process For the Preparation of Sulfomate-Carboxylate Derivatives
  申请人：Masui Toshiaki

  公开号：US20080262264A1

  公开（公告）日：2008-10-23

  Disclosed is a process for the preparation of Compound (III), salt or solvate thereof by reacting Compound (I), salt or solvate thereof with Compound (II) in a toluene solvent in the presence of an additive such as water or an alcohol. Also disclosed is a process for the preparation of Compound (IV) comprising hydrolyzing the obtained Compound (III) if necessary, and then oxidizing. In the formula, R 1 is hydrogen, optionally substituted lower alkyl, optionally substituted aryl or optionally substituted aryl lower alkyl, and R 2 is optionally substituted lower alkyl, optionally substituted cycloalkyl or optionally substituted aryl lower alkyl.
• PROCESS FOR THE PREPARATION OF SULFOMATE-CARBOXYLATE DERIVATIVES
  申请人：MASUI Toshiaki

  公开号：US20120010428A1

  公开（公告）日：2012-01-12

  Disclosed is a process for the preparation of Compound (III), salt or solvate thereof by reacting Compound (I), salt or solvate thereof with Compound (II) in a toluene solvent in the presence of an additive such as water or an alcohol. Also disclosed is a process for the preparation of Compound (IV) comprising hydrolyzing the obtained Compound (III) if necessary, and then oxidizing. In the formula, R 1 is hydrogen, optionally substituted lower alkyl, optionally substituted aryl or optionally substituted aryl lower alkyl, and R 2 is optionally substituted lower alkyl, optionally substituted cycloalkyl or optionally substituted aryl lower alkyl.