(S)-5-<(di-tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone | 148357-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (S)-5-<(di-tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone
• 英文别名: (S)-5-<(di-t-butoxycarbonyl)aminomethyl>-1-t-butoxycarbonyl-2-pyrrolidone；(S)-5-[(di-t-butoxycarbonyl)aminomethyl]-1-t-butoxycarbonyl-2-pyrrolidone
• CAS: 148357-98-6
• 化学式: C₂₀H₃₄N₂O₇
• 分子量: 414.499
• InChiKey: WIAOGHWIRLLHDY-ZDUSSCGKSA-N

物化性质

• 沸点：
  500.2±42.0 °C(predicted)
• 密度：
  1.139±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  102.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-5-<(di-tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone 在 氨 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以77%的产率得到(S)-N5,N5,N4-tri-t-butoxycarbonyl-4,5-diaminovaleramide
  参考文献：
  名称：

  Synthesis of chiral 1,2,4-triaminobutanes

  摘要：

  (S)-5-(Azidomethyl)-2-pyrrolidone, obtained by the Mitsunobu reaction, was reduced to (S)-5-(aminomethyl)-2-pyrrolidone which was hydrolysed to (S)-4,5-diaminovaleric acid. The acid, after acylation with i-butyl or with (1R, 3R, 4S)-menthyl chloroformate, underwent a Curtius reaction yielding the corresponding (S)-1,2-dialkoxycarbonyl-1,2,4-triaminobutane. Alternatively, (S)-5-(aminomethyl)-2-pyrrolidone was subjected to exhaustive t-butoxycarbonylation followed by ring-cleavage with ammonia to give (S)-N4,N5,N5-triboc-4,5-diaminovaleramide and was converted by a Hofmann rearrangement to (S)-N1,N2-di-t-butoxy carbonyl-4-methoxycarbonyl-1,2,4-triaminobutane.

  DOI：

  10.1016/s0957-4166(00)86019-x
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 palladium on activated charcoal 4-二甲氨基吡啶 、 锂硼氢 、 迭氮酸 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙腈 、 苯 为溶剂， -10.0~25.0 ℃ 、275.79 kPa 条件下， 反应 58.5h， 生成 (S)-5-<(di-tert-butoxycarbonyl)aminomethyl>-1-tert-butoxycarbonyl-2-pyrrolidone
  参考文献：
  名称：

  Synthesis of chiral 1,2,4-triaminobutanes

  摘要：

  (S)-5-(Azidomethyl)-2-pyrrolidone, obtained by the Mitsunobu reaction, was reduced to (S)-5-(aminomethyl)-2-pyrrolidone which was hydrolysed to (S)-4,5-diaminovaleric acid. The acid, after acylation with i-butyl or with (1R, 3R, 4S)-menthyl chloroformate, underwent a Curtius reaction yielding the corresponding (S)-1,2-dialkoxycarbonyl-1,2,4-triaminobutane. Alternatively, (S)-5-(aminomethyl)-2-pyrrolidone was subjected to exhaustive t-butoxycarbonylation followed by ring-cleavage with ammonia to give (S)-N4,N5,N5-triboc-4,5-diaminovaleramide and was converted by a Hofmann rearrangement to (S)-N1,N2-di-t-butoxy carbonyl-4-methoxycarbonyl-1,2,4-triaminobutane.

  DOI：

  10.1016/s0957-4166(00)86019-x

文献信息

• Selectively protected chiral 1,2,4-triaminobutanes and chiral vicinal 1,2-diamines
  作者：Janina Altman、Dov Ben-Ishai、Wolfgang Beck

  DOI：10.1016/s0957-4166(00)86240-0

  日期：1994.5

  Stepwise t-butoxycarbonylation of (S)-5-aminomethyl-2-pyrrolidone to mono-, di- and triacylated compounds has been elaborated. Ring opening of (S)-5-(Boc-aminomethyl)-N-1-Boc-2-pyrrolidone with LiOH afforded the Boc-protected 4,5-diaminovaleric acid, whereas with NaBH4 the Boc-protected (S)4,5-diamino-pentanol was obtained The acid underwent Curtius rearrangement to the corresponding isocyanate which was transformed to (S)-N-1,N-2-di-Boc-1,2,4-triaminobutane and to N-1,N-2-di-Boc-N-4-Z-triaminobutane. Curtius rearrangement of (S)-N-4,N-5-di-Z-valeric acid and pTSA catalyzed addition of t-BuOH to the isocyanate, yielded N-1,N-2-di-Z-N-4-Boc-1,2,4-triaminobutane.