(S)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate | 1601461-39-5

• 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)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (3S)-3-fluoro-3-[[(1R)-1-phenylethyl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 1601461-39-5
• 化学式: C₁₈H₂₅FN₂O₃
• 分子量: 336.407
• InChiKey: PFQFYBXOJSQFJB-ACJLOTCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate 在 dimethyl sulfide borane 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 60.0 ℃ 、3.04 MPa 条件下， 反应 32.0h， 生成 tert-butyl (3R)-3-(aminomethyl)-3-fluoropyrrolidine-1-carboxylate
  参考文献：
  名称：

  Convenient synthesis of enantiopure (R-) and (S-)-3-fluoro-3-aminomethylpyrrolidines

  摘要：

  (R-)- and (S-)-3-fluoro-3-aminomethylpyrrolidines were synthesized from methyl alpha-fluoroacrylate in eight steps. alpha-Phenylethylamine was used as a chiral auxiliary to separate the racemic mixture. The overall synthesis yield was 31%. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.002
• 作为产物：
  描述：

  1-(叔丁氧羰基)-3-氟吡咯烷-3-甲酸 、 R(+)-alpha-甲基苄胺 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以28%的产率得到(S)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS

  摘要：

  化合物的化学式（I）：为4-(3-氟-3-(2-(5,6,7,8-四氢-1,8-萘啶-2-基)乙基)吡咯烷-1-基)-3-(3-(2-甲氧基乙氧基)苯基)丁酸，或其盐。

  公开号：

  WO2016046225A1

文献信息

• NAPHTHYRIDINE DERIVATIVES AS ALPHA V BETA 6 INTEGRIN ANTAGONISTS FOR THE TREATMENT OF FIBROTIC DISEASES
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3428167A1

  公开（公告）日：2019-01-16

  A compound of formula (I): being 4-(3-Fluoro-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)-3-(3-(2-methoxyethoxy) phenyl) butanoic acid, or a salt thereof.

  式 (I) 的化合物： 4-(3-氟-3-(2-(5,6,7,8-四氢-1,8-萘啶-2-基)乙基)吡咯烷-1-基)-3-(3-(2-甲氧基乙氧基)苯基)丁酸或其盐。
• Compounds αvβ6 integrin antagonists
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：US10000489B2

  公开（公告）日：2018-06-19

  A compound of formula (I): wherein R is H or F; or a salt thereof.

  式 (I) 的化合物： 其中 R 是 H 或 F；或其盐。
• Determination of the absolute configuration of (+)- and (−)-N-CBZ-3-fluoropyrrolidine-3-methanol using vibrational circular dichroism and confirmation of stereochemistry by conversion to (R)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate
  作者：Panayiotis A. Procopiou、Richard J.D. Hatley、Sean M. Lynn、Royston C.B. Copley、Yanan He、Douglas J. Minick

  DOI：10.1016/j.tetasy.2016.09.008

  日期：2016.12

  Racemic N-CBZ-3-fluoropyrrolidine-3-methanol (+/-)-1 was resolved by preparative chiral HPLC. The absolute configuration of the enantiomers of 1 was identified by vibrational circular dichroism and confirmed by chemical synthesis, which involved exchanging the CBZ protecting group of (-)-1 with Boc, followed by oxidation with RuCl3, NaIO4, activation of the resulting acid with carbonyl diimidazole and reaction with (R)-alpha-methylbenzylamine to give (R)-tert-butyl 3-fiuoro-3-(((R)-1-phenylethyl)carbamoyl) pyrrolidine-l-carboxylate 7. The latter was compared with authentic (S)-tert-butyl 3-fluoro-3-(((R)-1phenylethyl)carbamoyl)pyrrolidine-l-carboxylate 6 and its diastereomer 7; the configuration of diastereomer 6 was obtained by an X-ray diffraction study. This established that the enantiomer (-)-1 had an (R)-configuration. (C) 2016 Elsevier Ltd. All rights reserved.
• NAPHTHYRIDINE DERIVATIVES AS ALPHA V BETA 6 INTEGRIN ANTAGONISTS FOR THE TREATMENT OF E.G. FIBROTIC DISEASES
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3197892B1

  公开（公告）日：2018-09-05
• NOVEL COMPOUNDS ALPHA v BETA 6 INTEGRIN ANTAGONISTS
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：US20170290817A1

  公开（公告）日：2017-10-12

  A compound of formula (I): which is 4-(3-fluoro-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)-3-(3-(2-methoxyethoxy)phenyl)butanoic acid, or a salt thereof.