4-甲氧基苄醇 → 1-(Tert-butyl)-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 525965笔记

反应方程式

HRID 525965 反应方程式
[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11](F)=[C:12](F)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([O:20]CC)=[O:19])=[CH:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-:23].[K+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][OH:32])=[CH:29][CH:28]=1>>[C:1]([N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:23][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)=[C:12]([O:32][CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[CH:13]=2)[C:8](=[O:17])[C:7]([C:18]([OH:20])=[O:19])=[CH:6]1)([CH3:2])([CH3:3])[CH3:4]

参与物

4

反应物 3

HCID 77384-甲氧基苄醇HCID 14797氢氧化钾HCID 14612522HCID 14612522，化合物

产物 1

HCID 867328301-(Tert-butyl)-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid收率 72.9%

反应条件

温度
80 °C

实验过程

A mixture of ethyl 1-(tert-butyl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (50 g, 162 mmol), KOH (136 g, 2425 mmol) and 4-methoxybenzyl alcohol (201 ml, 1617 mmol) was heated at 80° C. under N2 for 8 h. LCMS showed completion of reaction. The solution was adjusted to pH 2, extracted with EA and washed with water. The organic phase was concentrated in vacuo and the crude product was triturated in Et2O to afford 1-(tert-butyl)-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (61 g, 118 mmol, 72.9% yield) as pale yellow solid. LCMS: (M+H)+: 518.3.

后处理

  1. customcompletion of reaction
  2. extractionextracted with EA
  3. washwashed with water
  4. concentrationThe organic phase was concentrated in vacuo
  5. customthe crude product was triturated in Et2O

来源与证据

ORD记录
ord-ffe41d08de304743acd4c291b74f420a
来源数据集
uspto-grants-2016_05
专利号
US09340556B2

反应笔记

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