Hydrochloric Acid → 3-{[4-(Methoxycarbonyl)phenyl](methyl)sulfamoyl}benzoic acid

HRID 1025432Notes

Reaction equation

HRID 1025432 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH3:30])[S:12]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[C:18]([O:20]CC[Si](C)(C)C)=[O:19])(=[O:14])=[O:13])=[CH:7][CH:6]=1)=[O:4].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH3:30])[S:12]([C:15]2[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=2)[C:18]([OH:20])=[O:19])(=[O:13])=[O:14])=[CH:9][CH:10]=1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 712382762-(Trimethylsilyl)ethyl 3-{[4-(methoxycarbonyl)phenyl](methyl)sulfamoyl}benzoate

Product 1

HCID 682078793-{[4-(Methoxycarbonyl)phenyl](methyl)sulfamoyl}benzoic acidYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1.5 g of 2-(trimethylsilyl)ethyl 3-{[4-(methoxycarbonyl)phenyl](methyl)sulfamoyl}benzoate, a solution of TBAF in THF (1.0 M, 7.0 mL), and 15 mL of THF was stirred at room temperature for 2 hours. To the reaction mixture was added 0.2 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 0.2 M hydrochloric acid, water, and saturated brine in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1.11 g of 3-{[4-(methoxycarbonyl)phenyl](methyl)sulfamoyl}benzoic acid as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 0.2 M hydrochloric acid, water, and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aed5ac181d7842c08c067bf3bfd9bfa0
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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