(S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid | 129982-29-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid
• 英文别名: 1-[(2S)-2-[[bis[(1S)-1-phenylethyl]amino]methyl]-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]cyclopentane-1-carboxylic acid
• CAS: 129982-29-2
• 化学式: C₃₀H₄₁NO₄
• 分子量: 479.66
• InChiKey: FJHUBNIPEXRAHZ-FXSPECFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid 在 5%-palladium/activated carbon 、 氢气 、 1-羟基苯并三唑 、 苯甲醚 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 10.0~35.0 ℃ 、413.7 kPa 条件下， 反应 13.0h， 生成 山帕曲拉
  参考文献：
  名称：

  The Chemical Development and Scale-Up of Sampatrilat¹

  摘要：

  The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.

  DOI：

  10.1021/op020091f
• 作为产物：
  描述：

  tert-butyl 2-hydroxymethylacrylate 在 吡啶 、 氯化亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid
  参考文献：
  名称：

  The Chemical Development and Scale-Up of Sampatrilat¹

  摘要：

  The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.

  DOI：

  10.1021/op020091f

文献信息

• Asymmetric synthesis of β-amino acid derivatives by Michael addition to chiral 2-aminomethylacrylates
  作者：Ian T. Barnish、Martin Corless、Peter J. Dunn、David Ellis、Paul.W. Finn、J.David Hardstone、Keith James

  DOI：10.1016/s0040-4039(00)91786-6

  日期：1993.2

  The addition of lithium enolates to chiral aminomethylacrylates 7 and 8 proceeded with excellent diastereodifferentiation (up to 98% de) and provided an expeditious synthesis of homochiral β-aminomethylglutarates 9 and 10, on a scale of up to 500g. The acrylates 7 and 8, and their antipodes, should be useful synthons for the synthesis of β-amino acid derivatives.

  向手性氨基甲基丙烯酸酯7和8中添加烯醇锂进行出色的非对映体分化（高达98％de），并以最大500g的规模快速合成了手性β-氨基甲基戊二酸酯9和10。丙烯酸酯7和8及其对映体应该是合成β-氨基酸衍生物的有用的合成子。
• The Chemical Development and Scale-Up of Sampatrilat¹
  作者：Peter J. Dunn、Michael L. Hughes、Patricia M. Searle、Albert S. Wood

  DOI：10.1021/op020091f

  日期：2003.5.1

  The discovery and scale-up of two routes to sampatrilat are described. The first Chemical R and D route used a side product from another development project to accelerate drug supply and expedite the early development programme. The second, more efficient Chemical R and D route had the potential for commercialisation and used an environmentally friendly variant of the Baylis-Hillman reaction, and an asymmetric Michael addition as key steps. Full preparative details for the aminomethacrylate 4, a potentially useful chiral synthon, are given for the first time, along with full experimental details of the asymmetric Michael addition to make the chiral glutarate 5. Finally, a striking polymorph case history is described.