Hydrochloric Acid → 3-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid

HRID 555165Notes

Reaction equation

HRID 555165 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:13]2[CH:14]=[CH:15][C:16]3[O:20][C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)=[C:18]([C:28](=[O:31])[NH:29][CH3:30])[C:17]=3[CH:32]=2)[C:11]=1[CH3:12])[C:5]([O:7]C)=[O:6].[OH-].[Na+].Cl>CO.C1COCC1>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:19]2[O:20][C:16]3[CH:15]=[CH:14][C:13]([C:10]4[CH:9]=[C:4]([CH:3]=[CH:2][C:11]=4[CH3:12])[C:5]([OH:7])=[O:6])=[CH:32][C:17]=3[C:18]=2[C:28](=[O:31])[NH:29][CH3:30])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59275743HCID 59275743, compound

Product 1

HCID 592756533-(2-(4-Fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl 3-fluoro-5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-4-methylbenzoate (0.3 g, 0.68 mmol, 1 eq) in a 1:1 mixture of MeOH/THF at ambient temperature was added 5 eq. of NaOH and heated to 60° C. for 5 h. The mixture was cooled to ambient temperature and then cooled in an ice-water bath. It was acidified slowly with 1.5 N HCl and then concentrated. The mixture with white precipitates was diluted with water and filtered to get the solid. It is further washed with water and dried in vacuum. Yield: 0.2 g (60%). 1H NMR (400 MHz, DMSO-d6): δ 2.22 (s, 3H), 2.82-2.84 (d, 3H, J=4.6 Hz), 7.39-7.43 (m, 3H,), 7.61 (s, 1H), 7.66-7.70 (d, 1H, J=8.6 Hz), 7.66-7.70 (m, 1H), 7.78-7.80 (d, 1H, J=8.5 Hz), 8.01-8.03 (m, 2H), 8.49-8.51 (d, 1H, J=4.76 Hz), 13.2 (s, 1H). LCMS: (ES−) m/z=420.0 (M−H). CHROMOLITH® SpeedROD C18 (4.6×3.0 mm-5.0 μm). Mphase A: 10% CH3OH-90% H2O-0.1% TFA. Mphase B: 90% CH3OH-10% H2O-0.1% TFA. Flow: 5 ml/Min.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. temperaturecooled in an ice-water bath
  3. concentrationconcentrated
  4. customThe mixture with white precipitates
  5. additionwas diluted with water
  6. filtrationfiltered
  7. customto get the solid
  8. washIt is further washed with water
  9. customdried in vacuum

Sources & evidence

ORD record
ord-20fa05cf3c7a4bb9b79eace4f9f4eabb
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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