Hydrochloric Acid → 3-Bicyclo[2.2.1]hept-2-yl-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid
Reaction equation
C[O:2][C:3](=[O:28])[CH:4]([N:13]1[CH2:17][C:16]([O:18][C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=2[F:26])=[CH:15][C:14]1=[O:27])[CH2:5][CH:6]1[CH2:11][CH:10]2[CH2:12][CH:7]1[CH2:8][CH2:9]2.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:7]12[CH2:12][CH:10]([CH2:9][CH2:8]1)[CH2:11][CH:6]2[CH2:5][CH:4]([N:13]1[CH2:17][C:16]([O:18][C:19]2[C:20]([F:26])=[CH:21][CH:22]=[CH:23][C:24]=2[F:25])=[CH:15][C:14]1=[O:27])[C:3]([OH:28])=[O:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
In a flask was placed 3-bicyclo[2.2.1]hept-2-yl-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (87 mg, 0.22 mmol) dissolved in tetrahydrofuran (3 mL). To this mixture at 25° C. was added a solution of lithium hydroxide monohydrate (19 mg, 0.44 mmol) in water (3 mL) and stirred for 1 h at 25° C. The mixture was then treated with a 1N aqueous hydrochloric acid solution to pH=2 and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 3-bicyclo[2.2.1]hept-2-yl-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid (73 mg, 87%) as a yellow solid.
Workup
- customIn a flask was placed
- extractionextracted with ethyl acetate (3×20 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e561d592837c4a8cb54b060b4e4c61fb
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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