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>[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
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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 (1.82 g, 6.48 mmol) in tetrahydrofuran (15 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (8.4 mL, 1.0 M, 8.42 mmol). The mixture was stirred at 25° C. for 2 h then, acidified with 2N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate (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, (1.35 g, 75%) as a yellow solid.
Workup
- extractionThe mixture was extracted with ethyl acetate (2×30 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3076ccb33a944deda52543fb3135d5e9
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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