Sodium Hydroxide → 3-[[(4-Tert-butylphenyl)sulfonyl](methyl)amino]thiophene-2-carboxylic acid
Reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([O:23]C)=[O:22])[CH3:15])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O1CCOCC1.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:16]2[CH:20]=[CH:19][S:18][C:17]=2[C:21]([OH:23])=[O:22])[CH3:15])(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
In an appropriate microwave vessel, a solution of 56 (0.129 g; 0.35 mmol) in dioxane (2 mL) at 25° C. was added aqueous sodium hydroxide (1.5 mL; 3.0 mmol; 2M). The vessel was sealed and brought to 110° C. for 10 minutes via the Biotage Initiator Microwave Synthesizer. Upon cooling to 25° C., the mixture was diluted with water (10 mL) and washed with diethyl ether (5 mL). The aqueous layer was treated with concentrated hydrochloric acid to pH 1 and extracted with dichloromethane (2×20 mL). The organic layers were combined, washed with water (5×25 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield the title product (0.54 g).
Workup
- customThe vessel was sealed
- washwashed with diethyl ether (5 mL)
- additionThe aqueous layer was treated with concentrated hydrochloric acid to pH 1
- extractionextracted with dichloromethane (2×20 mL)
- washwashed with water (5×25 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-498cb5cc4dd44158b488cbddc0d1f5d1
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178699B2
Reaction notes
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