Citric Acid → 3-(4-{[2'-Methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoic acid

HRID 273397

反応式

HRID 273397 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36]C)=[O:35])=[CH:28][CH:27]=2)[CH:19]=1.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:5]=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[CH:30][CH:31]=2)[CH:19]=1

参加物

7

反応物 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58903135Methyl 3-(4-{[2'-methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoate

生成物 1

HCID 589031573-(4-{[2'-Methyl-4'-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoic acid収率 48%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 3-(4-{[2′-methyl-4′-(3-(pyridin-2-yl)propoxy)biphenyl-3-yl]methoxy}phenyl)propanoate (0.401 g, 0.809 mmol) in methanol (5 mL) and tetrahydrofuran (5 mL) was added 2 M aqueous sodium hydroxide solution (1.5 mL) and the mixture was stirred at room temperature for 75 hrs. Water was added to the reaction mixture, and the mixture was neutralized 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 (50% ethyl acetate/hexane-ethyl acetate) and recrystallized from ethyl acetate-hexane to give the title compound (0.186 g, yield 48%) as colorless prism crystals.

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 (50% ethyl acetate/hexane-ethyl acetate)
  6. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-7a1bdf52ca2f4b0b97a84b6b303cd15e
出典データセット
uspto-grants-2008_11
特許番号
US07456218B2

関連ノート

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