(S)-5-(tert-butoxycarbonylaminomethyl)-2-pyrrolidone | 148357-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-5-(tert-butoxycarbonylaminomethyl)-2-pyrrolidone
• 英文别名: (S)-5-(t-butoxycarbonylaminomethyl)-2-pyrrolidone；tert-Butyl (S)-((5-oxopyrrolidin-2-yl)methyl)carbamate；tert-butyl N-[[(2S)-5-oxopyrrolidin-2-yl]methyl]carbamate
• CAS: 148357-97-5
• 化学式: C₁₀H₁₈N₂O₃
• 分子量: 214.265
• InChiKey: QAZQYXLZGZFSRM-ZETCQYMHSA-N

物化性质

• 沸点：
  404.5±18.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-(tert-butoxycarbonylaminomethyl)-2-pyrrolidone 在 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium azide 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 、 苯 为溶剂， 反应 14.0h， 生成 (2S)-N¹,N²-di-tert-butoxycarbonyl-1,2,4-triaminobutane
  参考文献：
  名称：

  Selectively protected chiral 1,2,4-triaminobutanes and chiral vicinal 1,2-diamines

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(00)86240-0
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 palladium on activated charcoal 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 9.5h， 生成 (S)-5-(tert-butoxycarbonylaminomethyl)-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

• COMPOUND AS SMALL MOLECULE INHIBITOR PD-1/PD-L1 AND APPLICATION THEREOF
  申请人：Medshine Discovery Inc.

  公开号：EP4043461A1

  公开（公告）日：2022-08-17

  A biaryl compound. Specifically disclosed is a compound represented by formula (I) and a pharmaceutically acceptable salt thereof.

  一种双芳基化合物。具体公开的是由式(I)表示的化合物及其药学上可接受的盐。
• PD-L1 ANTAGONIST COMPOUND
  申请人：Adlai Nortye Biopharma Co., Ltd.

  公开号：EP4083032A1

  公开（公告）日：2022-11-02

  Provided are a compound of Formula (I) and a pharmaceutical composition thereof, as well as a method for using the compounds of Formula (I) to prevent and/or treat immune-related disorders.

  提供了化合物(I)及其制药组合物，以及使用化合物(I)预防和/或治疗免疫相关疾病的方法。
• [EN] PD-L1 ANTAGONIST COMPOUND<br/>[FR] COMPOSÉ ANTAGONISTE DE PD-L1<br/>[ZH] PD-L1拮抗剂化合物
  申请人：ADLAI NORTYE BIOPHARMA CO LTD

  公开号：WO2021129584A1

  公开（公告）日：2021-07-01

  提供了一种式（I）化合物及其药物组合物，以及使用式（I）化合物预防和/或治疗免疫相关病症的方法。
• Synthesis of chiral 1,2,4-triaminobutanes
  作者：Janina Altman、Dov Ben-Ishai

  DOI：10.1016/s0957-4166(00)86019-x

  日期：1993.1

  (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.
• 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.