Sodium Hydroxide → HCID 86721894, compound

HRID 1049050Notes

Reaction equation

HRID 1049050 reaction equation
C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([S:10](=[O:24])(=[O:23])[N:11]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:25])=[O:2])=[CH:5][CH:6]=2)(=[O:23])=[O:24])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86721893HCID 86721893, compound

Product 1

HCID 86721894HCID 86721894, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[(4-fluoro-phenyl)-isobutyl-sulfamoyl]-benzoic acid methyl ester (1.05 g, 2.87 mmol) in MeOH (40 mL) was treated with 1 M aqueous NaOH (8.6 mL, 8.60 mmol) and stirred at room temperature for 2.5 hours. The MeOH was removed under vacuum, the aqueous a phase diluted with water, washed with EtOAc and acidified to pH 1-2 using 1 N aqueous HCl. The acidic aqueous was extracted with EtOAc. The combined extracts were dried over Na2SO4 and concentrated under vacuum to give 4-[(4-fluoro-phenyl)-isobutyl-sulfamoyl]-benzoic acid (914 mg, 91%). 1H NMR (300 MHz, DMSO) δ 13.48 (br s, 1H), 8.10 (d, J=8.3 Hz, 2H), 7.65 (d, J=8.3 Hz, 2H), 7.25-7.05 (m, 4H), 3.35 (d, J=7.3 Hz, 2H), 1.51-1.33 (m, 1H), 0.85 (d, J=6.6 Hz, 6H). LCMS (m/z, Method A) ES+ 352.0 [M+1]+.

Workup

  1. customThe MeOH was removed under vacuum
  2. additionthe aqueous a phase diluted with water
  3. washwashed with EtOAc
  4. extractionThe acidic aqueous was extracted with EtOAc
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-947a9801c6c945db9ae88f99f67f05e1
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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