methyl 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}oxy)phenyl]propanoate → 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}oxy)phenyl]propanoic acid

HRID 2110888Notes

Reaction equation

HRID 2110888 reaction equation
[C:1]1([C:7]2[N:8]([CH2:16][C:17]3[CH:36]=[CH:35][C:20]([CH2:21][O:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33]C)=[O:32])=[CH:25][CH:24]=4)=[CH:19][CH:18]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.O1CCCC1.[OH-].[Na+].C(OCC)(=O)C>[C:1]1([C:7]2[N:8]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([CH2:21][O:22][C:23]4[CH:24]=[CH:25][C:26]([CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:28]=4)=[CH:35][CH:36]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 1

HCID 23159895methyl 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}oxy)phenyl]propanoate

Product 1

HCID 116267723-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}oxy)phenyl]propanoic acidYield 90.3%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-[4-({4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}oxy)phenyl]propanoate (0.17 g, 0.36 mmol) was dissolved in a mixed solution of methanol (4 mL) and tetrahydrofuran (8 mL), and 1 N aqueous sodium hydroxide solution (0.71 mL) was added with stirring at room temperature. The mixture was stirred at the same temperature for 2 hr. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the mixture washed successively with 5% aqueous potassium hydrogensulfate solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from hexane/ethyl acetate=4/1 to give the title compound (0.15 g, yield 88%) as colorless crystals. MS (APCI−): 460 (M−H), 1H NMR (CDCl3) δ: 2.63 (2H, t, J=7.8 Hz), 2.89 (2H, t, J=7.8 Hz), 4.97 (2H, s), 5.36 (2H, s), 6.65 (1H, s), 6.87 (2H, d, J=8.7 Hz), 7.03 (2H, d, J=8.1 Hz), 7.07-7.19 (5H, m), 7.28-7.47 (7H, m), 7.67 (1H, m).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at the same temperature for 2 hr
  3. customAfter completion of the reaction
  4. washthe mixture washed successively with 5% aqueous potassium hydrogensulfate solution, water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from hexane/ethyl acetate=4/1

Sources & evidence

ORD record
ord-f63c2b4d6ff44c8e9393127ce5b019c7
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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