Hydrochloric Acid → 3-Bicyclo[2.2.1]hept-7-yl-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid
Reaction equation
C[O:2][C:3](=[O:27])[CH:4]([N:13]1[CH2:17][C:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:15][C:14]1=[O:26])[CH2:5][CH:6]1[CH:10]2[CH2:11][CH2:12][CH:7]1[CH2:8][CH2:9]2.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:7]12[CH:6]([CH2:5][CH:4]([N:13]3[CH2:17][C:16]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])=[CH:15][C:14]3=[O:26])[C:3]([OH:27])=[O:2])[CH:10]([CH2:9][CH2:8]1)[CH2:11][CH2:12]2Participants
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-7-yl-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (35 mg, 0.089 mmol) in tetrahydrofuran (2 mL). To this mixture at 25° C. was added a solution of lithium hydroxide monohydrate (8 mg, 0.18 mmol) in water (2 mL) and stirred for 1.5 h at 25° C. The mixture was treated with a 1N aqueous hydrochloric acid solution to pH=2 and was 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-7-yl-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid (32 mg, 97%) as a white solid.
Workup
- customIn a flask was placed
- extractionwas extracted 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-ee4a98e2d5de4d5b859beb900206aa7c
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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