Sodium Hydroxide → 4-(N-(3-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoic acid

HRID 2094892Notes

Reaction equation

HRID 2094892 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[OH-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[CH2:5][N:6]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[S:7]([C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57422336Methyl 4-(N-(3-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate

Product 1

HCID 252053574-(N-(3-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoic acidYield 31.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl 4-(N-(3-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate (500 mg, 1.12 mmol) was dissolved in MeOH/THF (1:1, 40 mL) and treated with a solution of aqueous NaOH (10 N, 8 ml). The mixture was stirred at ambient temperature overnight, then MeOH and THF were removed by rotary evaporation. The resulting aqueous solution was washed with EtOAc (10 mL) and acidified with 6 N aq HCl (˜15 mL) to pH˜4. The aqueous solution was extracted with EtOAc (3×, 40 mL) and the combined organic layers were washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified by recrystallization from EtOH to afford the title compound 4-(N-(3-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoic acid as a white crystalline solid (150 mg) in 30% yield.

Workup

  1. customMeOH and THF were removed by rotary evaporation
  2. washThe resulting aqueous solution was washed with EtOAc (10 mL)
  3. extractionThe aqueous solution was extracted with EtOAc (3×, 40 mL)
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was purified by recrystallization from EtOH

Sources & evidence

ORD record
ord-cb295ffef8064100a48f8bd6a70c03a3
Source dataset
uspto-grants-2013_05
Patent number
US08445692B2

Reaction notes

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