Hydrochloric Acid → 3-Phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoic acid

HRID 456815Notes

Reaction equation

HRID 456815 reaction equation
[C:1]1([CH2:7][CH:8]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]4[NH:25][C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:27][CH:28]=4)[CH:20]=3)[CH:15]=2)[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1>[C:1]1([CH2:7][CH:8]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([C:24]4[NH:25][C:26]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:27][CH:28]=4)[CH:20]=3)[CH:15]=2)[C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18439046methyl 3-phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoate

Product 1

HCID 115176673-Phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoic acidYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-phenyl-2-{[6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}propanoate (0.25 g, 0.56 mmol), prepared in the previous step, and 1N NaOH (1.1 mL, 1.1 mmol) in THF (25 mL) was stirred under nitrogen at ambient temperature overnight. By TLC analysis, starting material was still present. The mixture was heated to 60° C. for two hours, at which time no starting material remained. The mixture was cooled to ambient temperature, acidified with 1N HCl (2 mL) and the volatiles were removed under reduced pressure (without the application of heat). The residue was slurried with water, the solids filtered and washed with water. The solids were dissolved in methylene chloride, the solution dried (MgSO4), filtered and the solvent removed under reduced pressure to give the title compound as an off-white solid (0.22 g, 90%), mp 176–178° C. Elemental Analysis for C29H23NO3 Calc'd: C, 80.35; H, 5.35; N, 3.23. Found: C, 79.19; H, 5.31; N, 2.97.

Workup

  1. temperatureThe mixture was heated to 60° C. for two hours, at which time no starting material
  2. temperatureThe mixture was cooled to ambient temperature
  3. customthe volatiles were removed under reduced pressure (without the application
  4. temperatureof heat)
  5. filtrationthe solids filtered
  6. washwashed with water
  7. dissolutionThe solids were dissolved in methylene chloride
  8. dry with materialthe solution dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-78700c2f60354586a2c5f3b10f1c1aa7
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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