Sodium Hydroxide → HCID 59576663, compound

HRID 2059606Notes

Reaction equation

HRID 2059606 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[O:12][C:13]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:14]=3[C:15]=2[C:16](=[O:29])[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH:8]=[N:7]1)C.[OH-].[Na+:38]>C1COCC1.O>[CH3:35][O:34][C:32]1[CH:31]=[CH:30][C:14]2[C:15]([C:16](=[O:29])[C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)=[C:11]([C:9]3[CH:8]=[N:7][N:6]([CH2:5][C:4]([O-:36])=[O:3])[CH:10]=3)[O:12][C:13]=2[CH:33]=1.[Na+:38]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11720177HCID 11720177, compound

Product 1

HCID 59576663HCID 59576663, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of {4-[6-methoxy-3-(3,4,5-trimethoxy-benzoyl)-benzofuran-2-yl]-pyrazol-1-yl}-acetic acid ethyl ester (25 mg, 0.051 mmol) in a mixture of THF (1 mL) and water (1 mL) was added sodium hydroxide (70 mg, 1.75 mmol) and the reaction allowed to stir overnight at ambient temperature. After this time the reaction was concentrated under vacuum and the residue dissolved in water (20 mL) and washed with diethyl ether (5 mL). The aqueous layer was acidified to pH 1-2 with concentrated hydrochloric acid and extracted with ethyl acetate (2×15 mL). The combined organic layers were concentrated under vacuum, the residue was dissolved in methanol (2 mL) and the resulting solution was treated with a methanolic solution of sodium methoxide until a pH of 9 was obtained. The solvent was removed under vacuum and the resulting yellow solid was washed with small portions of cold diethyl ether and isopropanol to provide the title compound (22 mg, 89%). 1H-NMR (D2O) δ 7.48 (s, 1H), 7.28 (s, 1H), 6.68-6.60 (m, 2H), 6.60 (s, 2H), 6.28 (d, J=7.6 Hz, 1H), 4.49 (s, 2H), 3.61 (s, 3H), 3.49 (s, 3H), 3.39 (s, 6H).

Workup

  1. concentrationAfter this time the reaction was concentrated under vacuum
  2. dissolutionthe residue dissolved in water (20 mL)
  3. washwashed with diethyl ether (5 mL)
  4. extractionextracted with ethyl acetate (2×15 mL)
  5. concentrationThe combined organic layers were concentrated under vacuum
  6. dissolutionthe residue was dissolved in methanol (2 mL)
  7. additionthe resulting solution was treated with a methanolic solution of sodium methoxide until a pH of 9
  8. customwas obtained
  9. customThe solvent was removed under vacuum
  10. washthe resulting yellow solid was washed with small portions of cold diethyl ether and isopropanol

Sources & evidence

ORD record
ord-1e2d2d40ffd94faf993890d500f5fc10
Source dataset
uspto-grants-2012_10
Patent number
US08278290B2

Reaction notes

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