Hydrochloric Acid → 5-[3,5-Dichloro-4-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl]-thiophene-2-carboxylic acid
Reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[S:8][C:9]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([CH2:19][CH:20]3[CH2:24][CH2:23][N:22]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:21]3=[O:31])=[C:14]([Cl:32])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6].CCOC(C)=O.Cl>O1CCOCC1>[Cl:32][C:14]1[CH:13]=[C:12]([C:9]2[S:8][C:7]([C:5]([OH:6])=[O:4])=[CH:11][CH:10]=2)[CH:17]=[C:16]([Cl:18])[C:15]=1[CH2:19][CH:20]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:21]1=[O:31]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Add 1.0 mL of LiOH (2.0 N aq.) to a solution of 5-[3,5-Dichloro-4-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl]-thiophene-2-carboxylic acid methyl ester (85 mg, 0.182 mmol) in 3.0 mL of dioxane and heat to 50° C. After 3 hours, a TLC shows the reaction to be complete. Dilute the reaction with DCM /H2O (50/50), acidify with 1.0N HCl, extract with ethyl acetate, and dry the combined organic layers with sodium sulfate. Filter off the sodium sulfate and concentrate to give the title compound. LC/MS (API) m/z: 452.0 (M+1).
Workup
- customthe reaction
- additionDilute
- extractionextract with ethyl acetate
- dry with materialdry the combined organic layers with sodium sulfate
- filtrationFilter off the sodium sulfate
- concentrationconcentrate
Sources & evidence
- ORD record
- ord-5281614b7388400c99098fc838bf2d33
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713979B2
Reaction notes
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