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Dimethylformamide → (R)-2-[3-(2,4-dichlorobenzyl)-8-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]propionic Acid Methyl Ester

HRID 2266615
ノート
印刷プレビュー

反応式

HRID 2266615 の反応式
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[C:6](=[O:18])[NH:7][C:8]2[C:13]([C:14]=1[CH3:15])=[C:12]([OH:16])[CH:11]=[CH:10][C:9]=2[F:17].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[CH3:35][O:36][C:37](=[O:41])[C@@H:38](Cl)[CH3:39]>O>[CH3:35][O:36][C:37](=[O:41])[C@H:38]([O:16][C:12]1[CH:11]=[CH:10][C:9]([F:17])=[C:8]2[C:13]=1[C:14]([CH3:15])=[C:5]([CH2:4][C:3]1[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=1[Cl:1])[C:6](=[O:18])[NH:7]2)[CH3:39]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 135535Methyl 2-chloropropanoate, (S)-HCID 687858183-(2,4-dichlorobenzyl)-8-fluoro-5-hydroxy-4-methyl-1H-quinolin-2-one

生成物 1

HCID 68780097(R)-2-[3-(2,4-dichlorobenzyl)-8-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]propionic Acid Methyl Ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
45 °C

実験手順

A mixture of 3-(2,4-dichlorobenzyl)-8-fluoro-5-hydroxy-4-methyl-1H-quinolin-2-one (0.30 g), N,N-dimethylformamide (4.0 mL), potassium carbonate (0.13 g) and (S)-2-chloropropionic acid methyl ester (0.11 g) was stirred at 45° C. for 3 days. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 6:4 by volume) to afford title compound as a pale peach solid, 0.17 g.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 6:4 by volume)

出典と根拠

ORDレコード
ord-9cdfdefd189f4dbfade7af2ad48879d6
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07858640B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート