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

HRID 1943962Notes

Reaction equation

HRID 1943962 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 the mixture was 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. extractionthe mixture was extracted 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-bf3f6d888b984cfbbeb5ba865f559c02
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

Loading…