Tetrahydrofuran → 2,6-difluoro-3-(N-propylsulfamoylamino)benzoic acid

HRID 2196737Notes

Reaction equation

HRID 2196737 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:13]([NH:14][S:15](=[O:21])(=[O:20])[NH:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=[C:10]([F:22])[C:5]=1[C:6]([O:8]C)=[O:7].C1COCC1>CO>[F:3][C:4]1[C:13]([NH:14][S:15](=[O:20])(=[O:21])[NH:16][CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=[C:10]([F:22])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67088999methyl 2,6-difluoro-3-(N-propylsulfamoylamino)benzoate

Product 1

HCID 670888502,6-difluoro-3-(N-propylsulfamoylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (1M, 3.20 mL, 3.20 mmol) was added to methyl 2,6-difluoro-3-(N-propylsulfamoylamino)benzoate (0.24 g, 0.80 mmol) in 2:1 THF:MeOH (3 mL). The solution was stirred at room temperature for 16 hours, and then the solution was stirred at 70° C. for 16 hours. The solution was concentrated under reduced pressure to about half volume and then washed with EtOAc. The pH was adjusted to about 5 and extracted with EtOAc (3×5 mL). The organic layers were dried over sodium sulfate, decanted and concentrated to provide 2,6-difluoro-3-(N-propylsulfamoylamino)benzoic acid.

Workup

  1. stirringthe solution was stirred at 70° C. for 16 hours
  2. concentrationThe solution was concentrated under reduced pressure to about half volume
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc (3×5 mL)
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5041110c8cc54ee6ac7d772e4c92e215
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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