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

HRID 456844
Notes
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Reaction equation

HRID 456844 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH:29]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:30]([O:32]C)=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CO.O>C1COCC1>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH:29]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:30]([OH:32])=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962Water2×HCID 14798Sodium HydroxideHCID 18439042methyl 2-{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate

Product 1

HCID 114971282-{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acidYield 94%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent2×

Procedure

In a similar manner as described in step 2 of Example 12, the title compound was prepared from methyl 2-{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoate (0.186 g, 0.355 mmol), prepared in the previous step, and 1N NaOH (0.53 mL, 0.53 mmol) in 2:2:1 THF:MeOH:water (25 mL). The starting material required heating to dissolve in the THF (10 mL). After the solution was clear, MeOH (10 mL) was added followed by the water (5 mL). The reaction was complete after 2.5 hours. The solids were isolated by filtration to give 2-{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}-3-phenylpropanoic acid as a beige solid (0.17 g, 94%), mp 194–196° C. (dec). Elemental Analysis for C35H27NO3.0.23 H2O Calc'd: C, 81.83; H, 5.39; N, 2.73. Found: C, 81.07; H, 5.44; N, 2.56.

Workup

  1. temperatureThe starting material required heating
  2. customThe solids were isolated by filtration

Sources & evidence

ORD record
ord-455ab82f3163409383db289a4ae0a7a8
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes