Lithium Hydroxide → 2,6-Difluoro-3-(3-fluoropropylsulfonamido)benzoic acid

HRID 2196638Notes

Reaction equation

HRID 2196638 reaction equation
[F:1][C:2]1[C:10]([N:11]([S:18]([CH2:21][CH2:22][CH2:23][F:24])(=[O:20])=[O:19])S(CCC)(=O)=O)=[CH:9][CH:8]=[C:7]([F:25])[C:3]=1[C:4]([O-:6])=[O:5].[OH-].[Li+]>C1COCC1.CO.O>[F:1][C:2]1[C:10]([NH:11][S:18]([CH2:21][CH2:22][CH2:23][F:24])(=[O:19])=[O:20])=[CH:9][CH:8]=[C:7]([F:25])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 1317301202,6-Difluoro-3-(N-(3-fluoropropylsulfonyl)propylsulfonamido)benzoate

Product 1

HCID 580953432,6-Difluoro-3-(3-fluoropropylsulfonamido)benzoic acidYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2,6-Difluoro-3-(N-(3-fluoropropylsulfonyl)propylsulfonamido)benzoate (38 g, 120 mmol) was dissolved in 5:2 THF/MeOH (250 mL), and a solution of lithium hydroxide (8.77 g, 366 mmol) in water (50 mL) was added. The reaction mixture was stirred at room temperature for four hours. The majority of the organic solvents were then removed in vacuo. 2.5N HCl (500 mL) was slowly added to the mixture, and the resulting solid was filtered and rinsed with cold ether to give 2,6-difluoro-3-(3-fluoropropylsulfonamido)benzoic acid as a solid (29.3 g, 81% yield). 1H NMR (400 MHz, CDCl3 ppm) 9.85 (s, 1H), 7.54 (dt, 1H), 7.21 (dt, 1H), 4.54 (td, 2H), 2.20-2.00 (m, 2H), 3.24-3.18 (m, 2H).

Workup

  1. customThe majority of the organic solvents were then removed in vacuo
  2. addition2.5N HCl (500 mL) was slowly added to the mixture
  3. filtrationthe resulting solid was filtered
  4. washrinsed with cold ether

Sources & evidence

ORD record
ord-32c9caf4505d42ac8a3c73ac467786c6
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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