Sodium Hydroxide → 3-(Methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid
Reaction equation
[CH3:1][N:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14]C)=[O:13])[S:3]([CH3:6])(=[O:5])=[O:4].[OH-].[Na+]>C1COCC1.CO.O>[CH3:20][O:19][C:17]([C:9]1[CH:10]=[C:11]([CH:16]=[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[CH:8]=1)[C:12]([OH:14])=[O:13])=[O:18]Participants
5
Procedure
Dimethyl 5-(N-methylmethylsulfonamido)isophthalate (0.842 g, 2.8 mmol) was dissolved in THF:MeOH (1:1) (8 mL) and H2O (3 mL). Solid NaOH (0.112 g, 2.8 mmol) was added and stirred at room temperature for 18 h. The reaction mixture was concentrated under reduced pressure. Saturated NaHCO3 (10 mL) was added to the reaction mixture and extracted with toluene (to remove <10% unreacted starting material). The aqueous solution was acidified with dilute HCl (10%), extracted with EtOAc, and dried over anhydrous Na2SO4. The solvent was evaporated and dried under reduced pressure to give 3-(methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid as a white solid (75%, 0.598 g), which was used without further purification.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionSaturated NaHCO3 (10 mL) was added to the reaction mixture
- extractionextracted with toluene (to remove <10% unreacted starting material)
- extractionextracted with EtOAc
- dry with materialdried over anhydrous Na2SO4
- customThe solvent was evaporated
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-65840668ed584f76ab0e7955ecb0ed9f
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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