Benzyl 2,6-difluoro-3-(propane-1-sulfonamido)benzoate → 2,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acid

HRID 1261000Notes

Reaction equation

HRID 1261000 reaction equation
C([O:8][C:9](=[O:25])[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([NH:17][S:18]([CH2:21][CH2:22][CH3:23])(=[O:20])=[O:19])[C:11]=1[F:24])C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:24][C:11]1[C:12]([NH:17][S:18]([CH2:21][CH2:22][CH3:23])(=[O:19])=[O:20])=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[C:9]([OH:25])=[O:8]

Participants

4

Reactant 1

HCID 53396460Benzyl 2,6-difluoro-3-(propane-1-sulfonamido)benzoate

Product 1

HCID 461929232,6-Difluoro-3-[(propylsulfonyl)amino]benzoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 2,6-difluoro-3-(propane-1-sulfonylamino)-benzoic acid benzyl ester (44, 2.0 g, mmol) in methanol (30 mL) was added 20% palladium hydroxide on carbon (100 mg). The reaction was stirred under hydrogen at 1 atm for 15 minutes. The reaction was filtrated and concentrated to give white solid 45 that was used in the next step.

Workup

  1. filtrationThe reaction was filtrated
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d4856cb64fca4e9eafe059260e501f50
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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