N2-[(2R)-2-氯丙酰基]-L-谷氨酰胺 | 159141-33-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酰胺类衍生物
• 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
• 中文名称: N2-[(2R)-2-氯丙酰基]-L-谷氨酰胺
• 中文别名: D-2-氯丙酰-L-谷氨酰胺；D-2-氯丙酰基-L-谷氨酰胺
• 英文名称: 2-chloropropionyl-L-glutamine
• 英文别名: 2-chloropropionyl glutamine；(S)-5-Amino-2-((R)-2-chloropropanamido)-5-oxopentanoic acid；(2S)-5-amino-2-[[(2R)-2-chloropropanoyl]amino]-5-oxopentanoic acid
• CAS: 159141-33-0
• 化学式: C₈H₁₃ClN₂O₄
• 分子量: 236.655
• InChiKey: JAKFXLPGGKWCLJ-UHNVWZDZSA-N

物化性质

• 沸点：
  600.5±55.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险品运输编号：
  1759
• 危险性描述：
  H302,H314
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  N2-[(2R)-2-氯丙酰基]-L-谷氨酰胺 在 ammonium hydroxide 作用下， 反应 9.0h， 以42.5 g的产率得到L-丙氨酰-L-谷氨酰胺
  参考文献：
  名称：

  Process Research and Development of l-Alanyl-l-glutamine, a Component of Parenteral Nutrition

  摘要：

  A large-scale manufacturing method of L-alanyl-L-glutamine used for a component of parenteral nutrition has been studied. The method consisted of a reaction of D-2-chloro- or D-2-bromopropionic acid with thionyl chloride and Schotten-Baumann reaction with L-glutamine followed by ammonolysis reaction. The intermediate D-2-chloropropionyl-L-glutamine was found to be more stable than its bromo analogue. In the ammonolysis reaction, the former intermediate needed a higher reaction temperature, but the by-products produced had little effect on the quality of the final product, The structures of the by-products were conjectured mainly by mass spectrometry and they were removed by anion resin treatment and recrystallization.

  DOI：

  10.1021/op990079w
• 作为产物：
  描述：

  (2R)-2-氯丙酰氯 、 L-谷氨酰胺 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 1.33h， 生成 N2-[(2R)-2-氯丙酰基]-L-谷氨酰胺
  参考文献：
  名称：

  一种氯丙酰谷氨酰胺的生产工艺

  摘要：

  本发明涉及化工技术领域，且公开了一种氯丙酰谷氨酰胺的生产工艺，包括以下步骤，酰氯化反应：以D‑2‑氯丙酸、二氯亚砜为原料，以DMF(N，N‑二甲基甲酰胺)为催化剂，反应生成D‑2‑氯丙酰氯、二氧化硫和氯化氢。该氯丙酰谷氨酰胺的生产工艺，通过氮气将791kg二氯亚砜压入干燥、洁净的2000L搪瓷反应釜中，开动搅拌，缓慢滴入N、N‑二甲基甲酰胺0.75kg。再通过氮气将600kg D‑2‑氯丙酸压入干燥、洁净的1000L搪瓷高位罐，反应釜夹套通75℃热水浴，将体系升温至60‑65℃，60‑65℃环境下，向反应釜内滴加D‑2‑氯丙酸，约4h滴完，通过调整滴加速度控制放气量，本方法步骤简单，反应物反应完全，原料利用率高，制备成本低，免去了使用者的烦恼，方便了使用者的使用。

  公开号：

  CN110845351A

文献信息

• Recovery of Ammonia in the Dipeptide Manufacturing Processes
  作者：Satoshi Kato、Takahiro Sano、Toru Sugaya

  DOI：10.1021/op000094x

  日期：2001.3.1

  An example of an improvement in recovering ammonia in a dipeptide manufacturing process is described. The synthetic method, which makes use of the ammonolysis reaction, has been studied and found to produce dipeptides of satisfactory quality in high yield on a large scale. However, the treatment of unreacted ammonia in the ammonolysis reaction caused a reduction in the productivity and increased the production cost during actual manufacture, Therefore, a method to recover the unreacted ammonia has been investigated through simulations and trial runs using model solutions, Consequently, the modified process provided an improvement in the productivity and cost savings. In addition, the recovered ammonia could possibly be used for recycling. It was verified in a lab experiment that the reused ammonia did not lower the quality of the dipeptide.
• Process Research and Development of <scp>l</scp>-Alanyl-<scp>l</scp>-glutamine, a Component of Parenteral Nutrition
  作者：Takahiro Sano、Toru Sugaya、Kunimi Inoue、Sho-ichi Mizutaki、Yasuyuki Ono、Masaji Kasai

  DOI：10.1021/op990079w

  日期：2000.5.1

  A large-scale manufacturing method of L-alanyl-L-glutamine used for a component of parenteral nutrition has been studied. The method consisted of a reaction of D-2-chloro- or D-2-bromopropionic acid with thionyl chloride and Schotten-Baumann reaction with L-glutamine followed by ammonolysis reaction. The intermediate D-2-chloropropionyl-L-glutamine was found to be more stable than its bromo analogue. In the ammonolysis reaction, the former intermediate needed a higher reaction temperature, but the by-products produced had little effect on the quality of the final product, The structures of the by-products were conjectured mainly by mass spectrometry and they were removed by anion resin treatment and recrystallization.
• 一种氯丙酰谷氨酰胺的生产工艺
  申请人：安徽生源化工有限公司

  公开号：CN110845351A

  公开（公告）日：2020-02-28

  本发明涉及化工技术领域，且公开了一种氯丙酰谷氨酰胺的生产工艺，包括以下步骤，酰氯化反应：以D‑2‑氯丙酸、二氯亚砜为原料，以DMF(N，N‑二甲基甲酰胺)为催化剂，反应生成D‑2‑氯丙酰氯、二氧化硫和氯化氢。该氯丙酰谷氨酰胺的生产工艺，通过氮气将791kg二氯亚砜压入干燥、洁净的2000L搪瓷反应釜中，开动搅拌，缓慢滴入N、N‑二甲基甲酰胺0.75kg。再通过氮气将600kg D‑2‑氯丙酸压入干燥、洁净的1000L搪瓷高位罐，反应釜夹套通75℃热水浴，将体系升温至60‑65℃，60‑65℃环境下，向反应釜内滴加D‑2‑氯丙酸，约4h滴完，通过调整滴加速度控制放气量，本方法步骤简单，反应物反应完全，原料利用率高，制备成本低，免去了使用者的烦恼，方便了使用者的使用。