Sodium Hydroxide → HCID 58095355, compound

HRID 1943851Notes

Reaction equation

HRID 1943851 reaction equation
[OH-].[Na+].[CH:3]1([CH2:6][S:7]([N:10]([C:18]2[C:19]([F:28])=[C:20]([C:24]([F:27])=[CH:25][CH:26]=2)[C:21]([OH:23])=[O:22])S(CC2CC2)(=O)=O)(=[O:9])=[O:8])[CH2:5][CH2:4]1>C1COCC1.CO>[CH:3]1([CH2:6][S:7]([NH:10][C:18]2[C:19]([F:28])=[C:20]([C:24]([F:27])=[CH:25][CH:26]=2)[C:21]([OH:23])=[O:22])(=[O:8])=[O:9])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131730119HCID 131730119, compound

Product 1

HCID 58095355HCID 58095355, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 1N NaOH (2.78 mL, 2.78 mmol) was added to a solution of crude 3-(1-cyclopropyl-N-(cyclopropylmethylsulfonyl)methylsulfonamido)-2,6-difluorobenzoic acid (380 mg, 0.928 mmol) in 4:1 THF/MeOH (5 mL, 0.2M). The reaction mixture was stirred at room temperature for 1 hour, after which most of the organic solvents were removed. 1N HCl (3 mL) was slowly added to the mixture to acidify to a pH of 1. The acidified aqueous layer was extracted with ethyl acetate (75 mL). The ethyl acetate extract was washed with water (2×20 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated. Trituration of the residue with Et2O afforded 3-(cyclopropylmethylsulfonamido)-2,6-difluorobenzoic acid as a solid (139 mg, 51%). 1H NMR (400 MHz, d6-DMSO) δ 9.76 (s, 1H), 7.60-7.54 (m, 1H), 7.22-7.16 (m, 1H), 3.10 (d, J=7.0 Hz, 2H), 1.10-0.99 (m, 1H), 0.58-0.53 (m, 2H), 0.36-0.31 (m, 2H); m/z (APCI-neg) M-1=289.9.

Workup

  1. customafter which most of the organic solvents were removed
  2. addition1N HCl (3 mL) was slowly added to the mixture
  3. extractionThe acidified aqueous layer was extracted with ethyl acetate (75 mL)
  4. extractionThe ethyl acetate extract
  5. washwas washed with water (2×20 mL), brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5b0fdd972eff4d00b97e0b093c00ae09
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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