Potassium Hydroxide → HCID 23159897, compound

HRID 2110880Notes

Reaction equation

HRID 2110880 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=3)[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])=[CH:24][CH:23]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.[OH-].[K+]>O1CCCC1.CO.C(OCC)(=O)C>[NH:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:18]=[C:19]([CH:34]=[CH:35][CH:36]=3)[CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[CH:24][CH:23]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 23159915HCID 23159915, compound

Product 1

HCID 23159897HCID 23159897, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-(4-{[3-(1-tert-butoxycarbonyl-1H-indol-5-yl)benzyl]oxy}phenyl)propanoate (3.8 g, 7.83 mmol) was dissolved in a mixed solvent of tetrahydrofuran (30 mL) and methanol (30 mL), and the mixture was ice-cooled. An aqueous solution (10 mL) of 85% potassium hydroxide (1.0 g, 15.1 mmol) was added to the solution, and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, and the mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained oil was crystallized from diethyl ether-hexane to give 3-(4-{[3-(1H-indol-5-yl)benzyl]oxy}phenyl)propanoic acid (2.2 g, yield 76%) as colorless needle crystals. MS: m/z 372 (MH+).

Workup

  1. temperaturecooled
  2. washthe mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained oil was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-b5cdd7970363427787844a679b2fe4dd
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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