Water → 3-(4-Tert-butylphenylsulfonamido)thieno[2,3-b]pyridine-2-carboxylic acid
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[C:24]([O:26]C)=[O:25])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[C:24]([OH:26])=[O:25])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 94 (0.070 g; 0.17 mmol) in tetrahydrofuran (2 mL), aqueous sodium hydroxide (2 mL; 4 mmol; 2N) and water (4 mL) were added. The reaction mixture was heated at 50° C. for 5 hours, cooled to room temperature, and then extracted with diethyl ether (2×). The ether solution was discarded. The aqueous layer was acidified with aqueous hydrochloric acid (2N) and extracted with ethyl acetate. The organic layer was separated and washed with aqueous saturated sodium chloride, dried over magnesium sulfate filtered, and evaporated under reduced pressure to yield the title compound as an off-white solid (0.067 g).
Workup
- temperaturecooled to room temperature
- extractionextracted with diethyl ether (2×)
- extractionextracted with ethyl acetate
- customThe organic layer was separated
- washwashed with aqueous saturated sodium chloride
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-835f1beef9c04b598d579f8a5cef6595
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178699B2
Reaction notes
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