Hydrochloric Acid → HCID 23159994, compound

HRID 2110905Notes

Reaction equation

HRID 2110905 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:9]([CH2:18][C:19]3[CH:39]=[CH:38][C:22]([CH2:23][O:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35]C)=[O:34])=[C:27]([CH3:37])[CH:26]=4)=[CH:21][C:20]=3[O:40][CH:41]([CH3:43])[CH3:42])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.O1CCCC1.C(OCC)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:9]([CH2:18][C:19]3[CH:39]=[CH:38][C:22]([CH2:23][O:24][C:25]4[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[C:27]([CH3:37])[CH:26]=4)=[CH:21][C:20]=3[O:40][CH:41]([CH3:43])[CH3:42])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23159981HCID 23159981, compound

Product 1

HCID 23159994HCID 23159994, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a mixed solution of methyl 3-[4-({4-[(3,5-diphenyl-1H-pyrazol-1-yl)methyl]-3-isopropoxybenzyl}oxy)-2-methylphenyl]propanoate (0.20 g, 0.35 mmol) in methanol (2 mL) and tetrahydrofuran (4 mL) was added 1 N aqueous sodium hydroxide solution (0.70 mL, 0.70 mmol), and the mixture was stirred at 50° C. 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 preparative HPLC (gradient cycle A). The obtained oil was diluted with ethyl acetate, and neutralized with saturated aqueous sodium hydrogencarbonate, and the mixture washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (0.15 g, yield 77%) as a colorless oil. MS (ESI+): 561 (M+H).

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 preparative HPLC (gradient cycle A)
  5. additionThe obtained oil was diluted with ethyl acetate
  6. washthe mixture washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb5d53cc231045a6919be7f8e05891a5
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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