Methanol → 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoic acid

HRID 456833Notes

Reaction equation

HRID 456833 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[N:25]([CH2:35][C:36]5[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=5)[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+].C1COCC1.CO>O>[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[N:25]([CH2:35][C:36]5[CH:37]=[CH:38][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:40][CH:41]=5)[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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 18439045methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoate

Product 1

HCID 116572213-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoic acidYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoate (0.200 g, 0.330 mmol), prepared in the previous step, and 1N NaOH (0.50 mL, 0.50 mmol) in 1.33:1.33:1 THF:MeOH:water (33 mL) with the exception that this reaction was not complete after 18 hours (overnight) at ambient temperature. The reaction was warmed to 30° C. for 1.5 hours, an additional portion of 1N NaOH (0.50 mL, 0.50 mmol) was added and the mixture maintained at 30° C. for an additional 1.5 hours. The isolated yellow amorphous solid was purified by reverse-phase (C18) HPLC using 20% water in acetonitrile with 0.1% formic acid as the eluent. Isolation of the product from the chromatography fractions gave 3-phenyl-2-[(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]propanoic acid as a greenish amorphous solid (0.139 g, 71%), mp 153–155° C. Elemental Analysis for C37H28F3NO3.0.24 H2O.0.10 C6H14 Calc'd: C, 74.70; H, 4.98; N, 2.32. Found: C, 74.67; H, 5.23; N, 2.25.

Workup

  1. custom(overnight)
  2. customat ambient temperature
  3. temperaturethe mixture maintained at 30° C. for an additional 1.5 hours
  4. customThe isolated yellow amorphous solid was purified by reverse-phase (C18) HPLC

Sources & evidence

ORD record
ord-a81d0c544fb8429fae25de6d369506dc
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

Loading…