Citric Acid → 3-[4-({[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid

HRID 508035ノート

反応式

HRID 508035 の反応式
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:24]([F:35])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:36])[CH:8]=1)[CH3:2].[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C.O1CCCC1>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:24]([F:35])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:36])[CH:8]=1)[CH3:2]

参加物

7

反応物 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23157676Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate

生成物 1

HCID 231572823-[4-({[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid収率 99.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 3-[4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate (2.88 g, 5.83 mmol) in a mixture of ethanol (90 mL) and tetrahydrofuran (90 mL) was added 2 M aqueous sodium hydroxide solution (30 mL), and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was weakly acidified with 10% aqueous citric acid solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) to give the title compound (2.70 g, yield 99%) as a pale-yellow oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-f77b027da7ab4e2a917f53d007bf159c
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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