Lithium Hydroxide → 3-[2-Bromo-4-(trifluoromethyl)phenylsulfonamido]thiophene-2-carboxylic acid
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21]([O:23]C)=[O:22])(=[O:14])=[O:13].[OH-].[Li+]>O1CCCC1.CO>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:5]=[CH:4][C:3]=1[S:12]([NH:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21]([OH:23])=[O:22])(=[O:14])=[O:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 77.5 °C
Procedure
To a solution of 97 (330.0 mg; 0.74 mmol) in tetrahydrofuran (8 mL) and methanol (2 mL) was added aqueous lithium hydroxide (4 mL; 2M). The reaction mixture was heated at 75-80° C. for 6 hours, allowed to cool to room temperature and then concentrated under reduced pressure. The resulting residue was dissolved in chloroform (15 mL) and washed with aqueous hydrochloric acid (2×10 mL; 2N). The organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by preparative HPLC to afford the title compound as a white solid (110 mg).
Workup
- temperatureto cool to room temperature
- concentrationconcentrated under reduced pressure
- dissolutionThe resulting residue was dissolved in chloroform (15 mL)
- washwashed with aqueous hydrochloric acid (2×10 mL; 2N)
- dry with materialThe organic phase was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by preparative HPLC
Sources & evidence
- ORD record
- ord-55868052b5554a7fbc3f726d4708967e
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178699B2
Reaction notes
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