(2S)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide | 342603-62-7

• 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)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
• CAS: 342603-62-7
• 化学式: C₇H₁₂F₃N₃O
• 分子量: 211.187
• InChiKey: VTWKCMKBSSXKLS-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  53.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide 在 三乙胺 作用下， 以 醋酸异丙酯 、 水 、 乙腈 为溶剂， 反应 66.5h， 生成 tert-butyl (3S)-4-{(2S,4R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-2-hydroxy-5-oxopentyl}-3-{[(2,2,2-trifluoroethyl)amino]carbonyl}piperazine-1-carboxylate
  参考文献：
  名称：

  Total synthesis of a second generation HIV protease inhibitor

  摘要：

  An efficient stereoselective preparation of HIV protease inhibitor (+)-1 was synthesized on multi-kilogram scale in 16 steps without the use of chromatography. The key steps include the diastereoselective alkylation of acetal 3, a diastereoselective iodo-hydroxylation to generate epoxide 6, and a reductive amination in the final coupling step that averts a non-productive Cyclic aminal intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.023
• 作为产物：
  描述：

  2-甲酸吡嗪 在 palladium dihydroxide 氢气 、 1-羟基苯并三唑 、 (+)-10-camphorsulfonic acid 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 10.0~73.0 ℃ 、275.79 kPa 条件下， 反应 10.0h， 生成 (2S)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide
  参考文献：
  名称：

  Total synthesis of a second generation HIV protease inhibitor

  摘要：

  An efficient stereoselective preparation of HIV protease inhibitor (+)-1 was synthesized on multi-kilogram scale in 16 steps without the use of chromatography. The key steps include the diastereoselective alkylation of acetal 3, a diastereoselective iodo-hydroxylation to generate epoxide 6, and a reductive amination in the final coupling step that averts a non-productive Cyclic aminal intermediate. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.09.023

文献信息

• Piperazine carboxamide intermediates of HIV protease inhibitors and processes for their preparation
  申请人：——

  公开号：US20030191121A1

  公开（公告）日：2003-10-09

  Piperazine carboxamide intermediates of HIV protease inhibitors and a process for their preparation are disclosed. The piperazine carboxamide compounds are of Formula (III): 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are defined herein. The process for preparing the intermediates comprises coupling an iminium salt of Formula I: 2 with a metallated derivative of a compound of Formula (II): R 1 —H  (II), wherein L − is a counterion. A process for preparing the iminium salt of Formula (I) is also disclosed, as is a process for preparing HIV protease inhibitors from Compound III.

  本文披露了HIV蛋白酶抑制剂的哌嗪羧酰胺中间体及其制备方法。哌嗪羧酰胺化合物的化学式为（III）：其中R1、R2、R3、R4、R5和R6的定义如本文所述。制备中间体的方法包括将化合物I的亚胺盐与化合物II的金属化衍生物偶联：其中化合物II的化学式为R1-H（II），其中L-是一个计数离子。本文还披露了制备化合物I的亚胺盐的方法，以及从化合物III制备HIV蛋白酶抑制剂的方法。
• Total synthesis of a second generation HIV protease inhibitor
  作者：Donald R. Gauthier、Norihiro Ikemoto、Fred J. Fleitz、Ronald H. Szumigala、Dan Petrillo、Jinchu Liu、Robert A. Reamer、Joseph D. Armstrong、Peter M. Yehl、Naijun Wu、R.P. Volante

  DOI：10.1016/j.tetasy.2003.09.023

  日期：2003.11

  An efficient stereoselective preparation of HIV protease inhibitor (+)-1 was synthesized on multi-kilogram scale in 16 steps without the use of chromatography. The key steps include the diastereoselective alkylation of acetal 3, a diastereoselective iodo-hydroxylation to generate epoxide 6, and a reductive amination in the final coupling step that averts a non-productive Cyclic aminal intermediate. (C) 2003 Elsevier Ltd. All rights reserved.