(2S)-1-(叔丁氧基羰基)-4-羟基吡咯烷-2-羧酸 → 4-(7-Methoxy-2-pyridin-2-yl-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic Acid 1-tert-butyl Ester

HRID 1815719

反应方程式

HRID 1815719 反应方程式
[C:1]([N:8]1[CH2:15][CH:14]([OH:16])[CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC([O-])(C)C.[K+].Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=2)[N:27]=[C:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[CH:25]=1>CS(C)=O.O>[C:4]([O:3][C:1]([N:8]1[CH2:15][CH:14]([O:16][C:24]2[C:33]3[C:28](=[CH:29][C:30]([O:34][CH3:35])=[CH:31][CH:32]=3)[N:27]=[C:26]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH:25]=2)[CH2:13][CH:9]1[C:10]([OH:12])=[O:11])=[O:2])([CH3:7])([CH3:6])[CH3:5]

参与物

6

反应物 3

HCID 11138980(2S)-1-(叔丁氧基羰基)-4-羟基吡咯烷-2-羧酸HCID 222502394-Chloro-7-methoxy-2-(pyridin-2-yl)quinolineHCID 23665647叔丁醇钾

产物 1

HCID 207736124-(7-Methoxy-2-pyridin-2-yl-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic Acid 1-tert-butyl Ester收率 51.3%

试剂、催化剂与溶剂 2

HCID 679二甲基亚砜溶剂2 次HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

实验过程

To a solution of N—Boc-4-hydroxyproline (1.6 g, 6.7 mmol) in DMSO (20 mL) was added t-BuOK (1.9 g, 16.8 mmol). The generated mixture was stirred for 1.5 h and 4-Chloro-7-methoxy-2-pyridin-2-yl-quinoline (2.0 g, 7.4 mmol) and DMSO (10 mL) were added. The reaction mixture was stirred for 38 h, diluted with cold water and extracted with EtOAc/ether (1/4, 2×). the aqueous layer was acidified to pH 4 and extracted with EtOAc/THF (5×). the combined extract was dried (Na2SO4/MgSO4), removed the solvent in vacuo and the residue was purified by preparative HPLC (0-80% solvent B) to provide the product (1.6 g, 50%): LC-MS (retention time: 1.23, Method I), MS m/z 466 (M++1).

后处理

  1. stirringThe reaction mixture was stirred for 38 h
  2. extractionextracted with EtOAc/ether (1/4, 2×)
  3. extractionextracted with EtOAc/THF (5×)
  4. extractionthe combined extract
  5. dry with materialwas dried (Na2SO4/MgSO4)
  6. customremoved the solvent in vacuo
  7. customthe residue was purified by preparative HPLC (0-80% solvent B)

来源与证据

ORD记录
ord-748f56009da046439c817ed64bd841a9
来源数据集
uspto-grants-2005_04
专利号
US06878722B2

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