Methanol → 2-{[6-(1-Methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

HRID 456830Notes

Reaction equation

HRID 456830 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][CH:4]=[C:3]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([O:23][CH:24]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:25]([O:27]C)=[O:26])[CH:17]=[CH:16]2.[OH-].[Na+].C1COCC1.CO>O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=[C:3]1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([O:23][CH:24]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:25]([OH:27])=[O:26])[CH:17]=[CH:16]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18439044methyl 2-{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 115396172-{[6-(1-Methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl 2-{[6-(1-methyl-5-phenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (0.200 g, 0.433 mmol), prepared in the previous step, and 1N NaOH (0.65 mL, 0.65 mmol) in 1.5:1.5:1 THF:MeOH:water (40 mL) with the exception that this reaction was complete after 18 hours (overnight) at ambient temperature. The title compound was isolated as a pale-yellow solid (0.194 g, 100%) and used without further purification, mp 171–173° C. Elemental Analysis for C30H25NO3.0.05 H2O Calc'd: C, 80.35; H, 5.64; N, 3.12. Found: C, 80.38; H, 5.67; N, 3.00.

Workup

  1. custom(overnight)
  2. customat ambient temperature

Sources & evidence

ORD record
ord-d28092703b1d43fa9ea6e2b54a5add2a
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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