Hydrochloric Acid → (S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid
Reaction equation
C[O:2][C:3](=[O:20])[C@@H:4]([N:12]1[CH2:16][C:15]([O:17][CH3:18])=[CH:14][C:13]1=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.O.[OH-].[Li+].Cl>O1CCCC1.O>[CH:6]1([CH2:5][C@H:4]([N:12]2[CH2:16][C:15]([O:17][CH3:18])=[CH:14][C:13]2=[O:19])[C:3]([OH:20])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution containing (S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (160 mg, 0.57 mmol) in tetrahydrofuran (3 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (26 mg, 1.08 mmol) in water (3 mL). The mixture was stirred at 25° C. for 2.5 h. The mixture was then acidified with 2N aqueous hydrochloric acid. The mixture was extracted with dichloromethane (2×30 mL). The combined organic layers were dried over magnesium sulfate and concentrated. To afford (S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid (145 mg, 95%) as an off-white solid.
Workup
- extractionThe mixture was extracted with dichloromethane (2×30 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a8d4bc202f1842c88eea1fb230f352dc
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
Loading…