Lithium hydroxide, monohydrate → (S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid
Reaction equation
C([O:3][C:4](=[O:25])[C@@H:5]([N:10]1[CH2:14][C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[C:17]=2[F:23])=[CH:12][C:11]1=[O:24])[CH2:6][CH:7]([CH3:9])[CH3:8])C.O.[OH-].[Li+]>O1CCCC1>[Br:22][C:18]1[C:17]([F:23])=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:15][C:13]1[CH2:14][N:10]([C@@H:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([OH:25])=[O:3])[C:11](=[O:24])[CH:12]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
To a solution containing (S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid ethyl ester (0.260 g, 0.63 mmol) in tetrahydrofuran (8 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 3 mL, 1.5 mmol). The mixture was stirred at 15° C. for 3 h, and the solvents evaporated. The residue was dissolved in water and washed with diethyl ether, and the diethyl ether layer discarded. The aqueous phase was acidified with dilute hydrochloric acid (pH <2), and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford (S)-2-[4-(3-bromo-2-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid, (0.250 g, 100%), as a yellow solid.
Workup
- customthe solvents evaporated
- dissolutionThe residue was dissolved in water
- washwashed with diethyl ether
- extractionextracted with ethyl acetate
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bb14228bf7204204a4fa539d2683da72
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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