(2S)-2-{[(1Z)-1-benzyl-3-oxo-3-piperidin-1-ylprop-1-en-1-yl]amino}-2-phenylacetamide | 679789-08-3

• 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: (2S)-2-{[(1Z)-1-benzyl-3-oxo-3-piperidin-1-ylprop-1-en-1-yl]amino}-2-phenylacetamide
• 英文别名: (2S)-2-[[(Z)-4-oxo-1-phenyl-4-piperidin-1-ylbut-2-en-2-yl]amino]-2-phenylacetamide
• CAS: 679789-08-3
• 化学式: C₂₃H₂₇N₃O₂
• 分子量: 377.486
• InChiKey: BSWXMTNVDAYDLL-DBJZRZIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-{[(1Z)-1-benzyl-3-oxo-3-piperidin-1-ylprop-1-en-1-yl]amino}-2-phenylacetamide 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以88%的产率得到(2S)-2-{[(1R)-1-benzyl-3-oxo-3-piperidin-1-ylpropyl]amino}-2-phenylacetamide
  参考文献：
  名称：

  Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives

  摘要：

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.

  DOI：

  10.1021/ja038812t
• 作为产物：
  描述：

  L-苯甘氨酰胺 、 4-oxo-1-phenyl-4-piperidin-1-ylbutan-2-one 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以35%的产率得到(2S)-2-{[(1Z)-1-benzyl-3-oxo-3-piperidin-1-ylprop-1-en-1-yl]amino}-2-phenylacetamide
  参考文献：
  名称：

  Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives

  摘要：

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.

  DOI：

  10.1021/ja038812t

文献信息

• [EN] PROCESS TO CHIRAL BETA-AMINO ACID DERIVATIVES<br/>[FR] PROCEDE DE SYNTHESE DE DERIVES D'ACIDES AMINES BETA CHIRAUX
  申请人：MERCK & CO INC

  公开号：WO2004085661A2

  公开（公告）日：2004-10-07

  The present invention relates to a process for the synthesis of chiral beta-amino acid derivatives and in particular to a process for the preparation of enantiomerically enriched beta-amino acid amide inhibitors of dipeptidyl peptidase-IV (DP-IV) which are useful for the treatment of Type 2 diabetes.

  本发明涉及一种手性β-氨基酸衍生物的合成过程，特别是一种制备对二肽基肽酶-IV（DP-IV）具有对映选择性的β-氨基酸酰胺抑制剂的方法，该抑制剂对2型糖尿病的治疗有用。
• Highly Diastereoselective Heterogeneously Catalyzed Hydrogenation of Enamines for the Synthesis of Chiral β-Amino Acid Derivatives
  作者：Norihiro Ikemoto、David M. Tellers、Spencer D. Dreher、Jinchu Liu、Angie Huang、Nelo R. Rivera、Eugenia Njolito、Yi Hsiao、J. Christopher McWilliams、J. Michael Williams、Joseph D. Armstrong、Yongkui Sun、David J. Mathre、Edward J. J. Grabowski、Richard D. Tillyer

  DOI：10.1021/ja038812t

  日期：2004.3.1

  Pure (Z)-enamines readily prepared from beta-ketoesters and amides using (S)-phenylglycine amide were hydrogenated with very high diastereoselectivities (up to 200:1) using heterogeneous catalysis. Hydrogenolytic cleavage of the (S)-phenylglycine amide afforded the corresponding chiral beta-aminoesters and amides. The high geometrical purity of the (Z)-enamine and a simple activation procedure for the PtO2 catalyst are essential in achieving high selectivity.