N-carbobenzoyloxy-N-ethyl-D-alanine | 1038919-34-4

• 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: N-carbobenzoyloxy-N-ethyl-D-alanine
• 英文别名: (2R)-2-{[(benzyloxy)carbonyl](ethyl)amino}propanoic acid；(2R)-2-[ethyl(phenylmethoxycarbonyl)amino]propanoic acid
• CAS: 1038919-34-4
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: BTEMZVZFHGLWJJ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-carbobenzoyloxy-N-ethyl-D-alanine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 20.0h， 生成 N-ethyl-D-alanine
  参考文献：
  名称：

  Synthesis of N-alkyl-N-methyl amino acids. Scope and limitations of base-induced N-alkylation of Cbz-amino acids

  摘要：

  The reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids with NaH/alkyl iodides gave the corresponding N-Cbz-N-alkyl derivatives in good to high yields. The scope and limitations of this simple N-alkylation reaction were investigated as a convenient and flexible attempt to prepare unsymmetrically N,N-diprotected alpha-amino acids. The procedure is based on the N-alkylation of N-carbamoyl amino acids, a one-pot deprotection/protection sequence without extensive purification of the products. Protection of the carboxyl function is not required while the starting materials are inexpensive and commercially available. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.025
• 作为产物：
  描述：

  N-benzyloxycarbonyl-D-alanine 、 碘乙烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到N-carbobenzoyloxy-N-ethyl-D-alanine
  参考文献：
  名称：

  Synthesis of N-alkyl-N-methyl amino acids. Scope and limitations of base-induced N-alkylation of Cbz-amino acids

  摘要：

  The reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids with NaH/alkyl iodides gave the corresponding N-Cbz-N-alkyl derivatives in good to high yields. The scope and limitations of this simple N-alkylation reaction were investigated as a convenient and flexible attempt to prepare unsymmetrically N,N-diprotected alpha-amino acids. The procedure is based on the N-alkylation of N-carbamoyl amino acids, a one-pot deprotection/protection sequence without extensive purification of the products. Protection of the carboxyl function is not required while the starting materials are inexpensive and commercially available. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.025

文献信息

• [EN] POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS<br/>[FR] ANTAGONISTES DE TLR7/8 POLYCYLIQUES ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES IMMUNES
  申请人：MERCK PATENT GMBH

  公开号：WO2017106607A1

  公开（公告）日：2017-06-22

  The present invention relates to compounds of Formula (I) and pharmaceutically acceptable compositions thereof, useful as toll-like receptor 7/8 (TLR7/8) antagonists. In Formula (I), Ring A is aryl or heteroaryl; Ring B is aryl or heteroary; and X is C(R4)2, O, NR4, S, S(R4), or S(R4)2.

  本发明涉及式(I)的化合物及其药学上可接受的组合物，作为Toll样受体7/8（TLR7/8）拮抗剂。在式(I)中，环A是芳基或杂芳基；环B是芳基或杂芳基；X是C(R4)2、O、NR4、S、S(R4)或S(R4)2。
• TLR7/8 antagonists and uses thereof
  申请人：Merck Patent GmbH

  公开号：US10399957B2

  公开（公告）日：2019-09-03

  The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TLR7/8 antagonists.

  本发明涉及可用作 TLR7/8 拮抗剂的式 I 化合物及其药学上可接受的组合物。
• POLYCYCLIC TLR7/8 ANTAGONISTS AND USE THEREOF IN THE TREATMENT OF IMMUNE DISORDERS
  申请人：Merck Patent GmbH

  公开号：EP3390389A1

  公开（公告）日：2018-10-24
• EP3889145A1
  申请人：——

  公开号：EP3889145A1

  公开（公告）日：2021-10-06
• EP3889146A1
  申请人：——

  公开号：EP3889146A1

  公开（公告）日：2021-10-06