Lithium Hydroxide → 2-[5-(3-Isopropyl-phenoxy)-4'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid
Reaction equation
C[O:2][C:3](=[O:35])[CH:4]([C:9]1[CH:10]=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[CH:17]=2)[CH:14]=1)[CH2:5][CH:6]([CH3:8])[CH3:7].C1COCC1.[Li+].[OH-]>CO>[CH:22]([C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:15][C:13]1[CH:14]=[C:9]([CH:4]([CH2:5][CH:6]([CH3:7])[CH3:8])[C:3]([OH:35])=[O:2])[CH:10]=[C:11]([C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=2)[CH:12]=1)([CH3:23])[CH3:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
A mixture of 2-[5-(3-isopropyl-phenoxy)-4′-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester (33 mg, 0.07 mmol), THF (0.6 mL), 10% aq. LiOH (0.2 mL) and MeOH (0.6 mL) was stirred at 30° C. for 3 h. The solution was concentrated and the residue was diluted with H2O (1 mL) and then acidified with conc HCl. The aqueous solution was extracted with DCM (3×1 mL) and the organic layers were filtered through PTFE filter. The solution was concentrated in vacuo to give a solid residue. The solid was purified using reverse phase preparative HPLC (MeCN, H2O) to afford the title compound (21.6 mg, 67%).
Workup
- concentrationThe solution was concentrated
- additionthe residue was diluted with H2O (1 mL)
- extractionThe aqueous solution was extracted with DCM (3×1 mL)
- filtrationthe organic layers were filtered through PTFE
- filtrationfilter
- concentrationThe solution was concentrated in vacuo
- customto give a solid residue
- customThe solid was purified
Sources & evidence
- ORD record
- ord-210d2b5c6a9b46f0ace5995b0b7ec125
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557244B2
Reaction notes
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