(1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-[(3S)-3-(L-prolylamino)-pyrrolidin-1-ylcarbonyl]-pyrrolidin-4-ylthio]1-carbapen-2-em-3-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-[(3S)-3-(L-prolylamino)-pyrrolidin-1-ylcarbonyl]-pyrrolidin-4-ylthio]1-carbapen-2-em-3-carboxylic acid
• 英文别名: (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(3S,5S)-5-[(3S)-3-[[(2S)-pyrrolidine-2-carbonyl]amino]pyrrolidine-1-carbonyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• 化学式: C₂₄H₃₅N₅O₆S
• 分子量: 521.638
• InChiKey: UYXZIZMBKDGZAK-VTGMPIQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  177
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (4-nitrophenyl)methyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(3S,5S)-1-[(4-nitrophenyl)methoxycarbonyl]-5-[(3S)-3-[[(2S)-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidine-2-carbonyl]amino]pyrrolidine-1-carbonyl]pyrrolidin-3-yl]sulfanyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 在 palladium on carbon 氢气 作用下， 生成 (1R,5S,6S)-6-[(1R)-1-hydroxyethyl]-1-methyl-2-[(2S,4S)-2-[(3S)-3-(L-prolylamino)-pyrrolidin-1-ylcarbonyl]-pyrrolidin-4-ylthio]1-carbapen-2-em-3-carboxylic acid
  参考文献：
  名称：

  Process for producing optically active 1H-3-aminopyrrolidine and derivatives thereof

  摘要：

  公开号：

  EP1188744B1

文献信息

• Process for producing 1H-3-aminopyrrolidine and derivatives thereof
  申请人：Mitsubishi Chemical Corporation

  公开号：US20020042523A1

  公开（公告）日：2002-04-11

  A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R′NH 2 , subjecting the reaction product to cyclodehydration to obtain an optically active 1 -aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

  公开了一种生产1H-3-氨基吡咯烷及其衍生物的方法。该方法特别适用于生产光学活性的1H-3-氨基吡咯烷及其衍生物，其中包括将公式（1）表示的光学活性氨基保护的天冬氨酸酐与公式R'NH2表示的一级胺反应，将反应产物经过环化脱水作用得到公式（2）表示的光学活性1-芳基甲基-3-(保护氨基)吡咯烷-2,5-二酮化合物，随后消除公式（2）所表示的化合物中3位氨基基团的保护基，得到公式（3）表示的光学活性1-芳基甲基-3-氨基吡咯烷-2,5-二酮化合物，将公式（3）所表示的化合物的羰基基团还原，得到公式（4）表示的光学活性1-芳基甲基-3-氨基吡咯烷化合物或其与质子酸的盐，然后将公式（4）所表示的化合物或其盐进行氢解，得到光学活性的1H-3-氨基吡咯烷或其质子酸盐。
• 1-METHYLCARBAPENEM DERIVATIVES
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0882728A1

  公开（公告）日：1998-12-09

  [Constitution] A 1-methylcarbapenem compound represented by the following formula (I): wherein R1 represents a hydrogen atom or a lower alkyl group; R2 represents a hydrogen atom or an ester residue; and A represents a substituted prolylaminopyrrolidin-1-ylcarbonyl, substituted aminoalkanoylaminopyrrolidin-1-ylcarbonyl, 1-hydroxy-2-(substituted aminoalkylpyrrolidin-1-ylcarbonyl)ethyl, 1-hydroxy-2-(substituted piperazin-1-ylcarbonyl)ethyl, 1-hydroxy-2-(substituted pyrrolidinylaminocarbonyl)ethyl or the like; or a pharmacologically acceptable salt thereof. [Advantages] 1-Methylcarbapenem compounds of the present invention have excellent antibacterial activity and they are useful agents for the prevention or treatment of infectious diseases.

  [组织结构］ 由下式(I)代表的1-甲基碳青霉烯类化合物： 其中 R1 代表氢原子或低级烷基；R2 代表氢原子或酯残基；A代表取代的脯氨酰氨基吡咯烷-1-基羰基、取代的氨基烷酰基氨基吡咯烷-1-基羰基、1-羟基-2-(取代的氨基烷基吡咯烷-1-基羰基)乙基、1-羟基-2-(取代的哌嗪-1-基羰基)乙基、1-羟基-2-(取代的吡咯烷氨基羰基)乙基或类似物；或其药理上可接受的盐。 优势 本发明的 1-甲基碳青霉烯化合物具有优异的抗菌活性，是预防或治疗传染性疾病的有效药物。
• Process for producing 1H-3-aminopyrrolidine and derivatives thereof
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1188744A1

  公开（公告）日：2002-03-20

  A process for producing 1H-3-aminopyrrolidine and derivatives thereof is disclosed. The process is especially useful for producing optically active 1H-3-aminopyrrolidine and derivatives thereof and in this case comprises reacting an optically active amino-protected aspartic anhydride represented by the formula (1) with a primary amine represented by the formula R'NH2, subjecting the reaction product to cyclodehydration to obtain an optically active 1-aralkyl-3-(protected amino)pyrrolidine-2,5-dione compound represented by the formula (2), subsequently eliminating the protective group from the 3-position amino group of the compound represented by the formula (2) to obtain an optically active 1-aralkyl-3-aminopyrrolidine-2,5-dione compound represented by the formula (3), reducing the carbonyl groups of the compound represented by the formula (3) to obtain either an optically active 1-aralkyl-3-aminopyrrolidine compound represented by the formula (4) or a salt thereof with a protonic acid, and then subjecting the compound represented by the formula (4) or the salt thereof to hydrogenolysis to obtain an optically active 1H-3-aminopyrrolidine or a protonic acid salt thereof.

  本发明公开了一种生产 1H-3-氨基吡咯烷及其衍生物的工艺。该工艺特别适用于生产具有光学活性的 1H-3-氨基吡咯烷及其衍生物，在这种情况下，该工艺包括将式（1）所代表的具有光学活性的氨基保护天冬氨酸酐与式 R'NH2 所代表的伯胺反应，使反应产物进行环脱水反应，得到式（2）所代表的具有光学活性的 1-烷基-3-（保护氨基）吡咯烷-2,5-二酮化合物、随后从式（2）代表的化合物的 3 位氨基上消除保护基团，得到式（3）代表的光学活性 1-烷基-3-氨基吡咯烷-2,5-二酮化合物、用质子酸还原式（3）所代表化合物的羰基，以获得光学活性的 1-烷基-3-氨基吡咯烷化合物（式（4）所代表）或其盐，然后将式（4）所代表化合物或其盐进行氢解，以获得光学活性的 1H-3- 氨基吡咯烷或其质子酸盐。
• US6531594B2
  申请人：——

  公开号：US6531594B2

  公开（公告）日：2003-03-11
• Process for producing optically active 1H-3-aminopyrrolidine and derivatives thereof
  申请人：MITSUBISHI CHEMICAL CORPORATION

  公开号：EP1188744B1

  公开（公告）日：2005-11-02