Hydrochloric Acid → HCID 23159992, compound

HRID 2110900Notes

Reaction equation

HRID 2110900 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:27]=[CH:26][C:11]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[N:5]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:3]=1.Cl>CO.O1CCCC1.[OH-].[Na+].O>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:16][CH:15]=3)=[CH:26][CH:27]=2)[N:5]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:3]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 23159903HCID 23159903, compound

Product 1

HCID 23159992HCID 23159992, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Methyl 3-[4-({4-[(5-methyl-3-phenyl-1H-pyrazol-1-yl)methyl]benzyl}oxy)phenyl]propanoate (220 mg, 0.5 mmol) was dissolved in a mixed solvent of methanol (3 mL) and tetrahydrofuran (3 mL), and 1 N aqueous sodium hydroxide solution (2 mL) was added. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with water, and neutralized with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (Manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4) to give the title compound (155 mg, yield 73%) as colorless crystals. 1H NMR (CDCl3) δ: 2.22 (3H, s), 2.64 (2H, t, J=7.5 Hz), 2.89 (2H, t, J=7.5 Hz), 5.00 (2H, s), 5.35 (2H, s), 6.38 (1H, s), 6.87 (2H, d, J=8.5 Hz), 7.07-7.18 (4H, m), 7.23-7.32 (1H, m), 7.33-7.44 (4H, m), 7.76-7.83 (2H, m).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1-1:4)

Sources & evidence

ORD record
ord-4125f44b5aa443e6a1e0d3e2d7f04c02
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

Loading…