Hydrochloric Acid → HCID 23159876, compound

HRID 2110903Notes

Reaction equation

HRID 2110903 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]2[CH:10]=[C:11]([CH:28]=[CH:29][C:30]=2[O:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])=[C:16]([F:27])[CH:15]=2)[N:3]=1.[OH-].[Na+].Cl>CO.O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][C:9]2[CH:10]=[C:11]([CH:28]=[CH:29][C:30]=2[O:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[C:16]([F:27])[CH:15]=2)[N:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23159917HCID 23159917, compound

Product 1

HCID 23159876HCID 23159876, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of ethyl 3-[4-({3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-isobutoxybenzyl}oxy)-2-fluorophenyl]propanoate (0.37 g, 0.77 mmol) in methanol (2 mL) and tetrahydrofuran (4 mL) was added 1 N aqueous sodium hydroxide solution (1.5 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was neutralized with 1 N hydrochloric acid, and diluted with ethyl acetate. The mixture washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/2) to give the title compound (0.25 g, yield 56%) as colorless crystals.

Workup

  1. washThe mixture washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-3c512ee25448447f846b1778bd9b7bc5
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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