Lithium Hydroxide → 3-[6-(4',5'-Difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid
Reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:25]=4[O:32][CH3:33])=[CH:20][CH:19]=3)[CH:14]=2)[CH:9]=[CH:8]1)C.O1CCCC1.[OH-].[Li+].O[Li].O>O>[F:31][C:27]1[C:28]([F:30])=[CH:29][C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][CH2:16][C:13]3[CH:14]=[C:15]4[C:10]([CH:9]=[CH:8][N:7]4[CH2:6][CH2:5][C:4]([OH:34])=[O:3])=[CH:11][CH:12]=3)=[CH:19][CH:20]=2)=[C:25]([O:32][CH3:33])[CH:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To 3-[6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid ethyl ester (24 mg, 0.051 mmol, 1 eq.) was added tetrahydrofuran (1 mL), water (1 mL) and lithium hydroxide (LiOH—H2O (4.5 mg, 0.1 mmol, 2.2 eq.). The reaction was stirred and at room temperature for 2 and then DOWEX resin (50WX4-400, acid washed, 2 g) was added. The mixture was stirred at room temperature, filtered, dried, and then lyophilized from acetonitrile/water to yield 3-[6-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid as an off-white solid (23 mg, 98%). LC-MS (ES) calculated for C25H21F2NO4, 437.12; found m/z 438 [M+H]+.
Workup
- washresin (50WX4-400, acid washed, 2 g)
- additionwas added
- stirringThe mixture was stirred at room temperature
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-c8840219c0794e679f640974af2b585c
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947728B1
Reaction notes
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