Methanol → [(6-{5-Phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]acetic acid
Reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([O:33][CH2:34][C:35]([O:37]C)=[O:36])[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C1COCC1.CO>O>[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)[C:10]([C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH:29]=[C:28]([O:33][CH2:34][C:35]([OH:37])=[O:36])[CH:27]=[CH:26]4)=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl [(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]acetate (0.20 g, 0.38 mmol), prepared in the previous step, and 1N NaOH (0.58 mL, 0.58 mmol) in 1.67:1.67:1 THF:MeOH:water (39 mL). Purification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å) using 25% EtOAc in hexane with 1% formic acid as the eluent gave [(6-{5-phenyl-1-[4-(trifluoromethyl)benzyl]-1H-pyrrol-2-yl}-2-naphthyl)oxy]acetic acid as an off-white solid (0.155 g, 79%), mp 154–156° C. Elemental Analysis for C30H22F3NO3.0.02 H2O Calc'd: C, 71.80; H, 4.43; N, 2.79. Found: C, 71.96; H, 4.55; N, 2.61.
Workup
- customPurification on a Biotage Horizon™ system with a KP-Sil Flash 25+M column (40 g Silica Gel, 60 Å)
Sources & evidence
- ORD record
- ord-387f1c55175a4c4cb6bd8358340899df
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186749B2
Reaction notes
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