Sodium Iodide → 3-[4-[[3-[Phenyl(propyl)amino]benzyl]oxy]phenyl]propanoic acid

HRID 2422311

反応式

HRID 2422311 の反応式
[NH:1]([C:8]1[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=1)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23]C)=[O:22])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:30](Br)[CH2:31][CH3:32].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:2]1([N:1]([CH2:30][CH2:31][CH3:32])[C:8]2[CH:9]=[C:10]([CH:25]=[CH:26][CH:27]=2)[CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:17][CH:18]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 57541953Methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate

生成物 1

HCID 575418483-[4-[[3-[Phenyl(propyl)amino]benzyl]oxy]phenyl]propanoic acid収率 48.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of methyl 3-[4-[(3-anilinobenzyl)oxy]phenyl]propanoate (0.20 g, 0.58 mmol) in N,N-dimethylformamide (4 mL) was added 60% sodium hydride (0.035 g, 0.86 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 10 min. n-Propylbromide (0.063 mL, 0.69 mmol) and sodium iodide (0.10 g, 0.69 mmol) were added to this mixture with stirring at 0° C., and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried, and concentrated under reduced pressure. Then the residue was dissolved in a mixed solution of methanol (3 mL) and tetrahydrofuran (6 mL), 1N aqueous sodium hydroxide solution (1.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was adjusted to pH 3 with 1N hydrochloric acid, separated and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-1/2) to give the title compound (0.11 g, yield 47%) as colorless crystals. MS (APCI−): 388 (M−H).

後処理

  1. additionwere added to this mixture
  2. stirringwith stirring at 0° C.
  3. stirringthe mixture was stirred at room temperature for 16 hrs
  4. washwashed with water and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThen the residue was dissolved in a mixed solution of methanol (3 mL) and tetrahydrofuran (6 mL), 1N aqueous sodium hydroxide solution (1.5 mL)
  8. additionwas added
  9. stirringthe mixture was stirred at room temperature for 1 hr
  10. customseparated
  11. extractionextracted with ethyl acetate
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-1/2)

出典と根拠

ORDレコード
ord-9ba4b6a7577342c2918738846e764f38
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

関連ノート

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