Hydrochloric Acid → [3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazol-4-yl]acetic acid

HRID 2221630Notes

Reaction equation

HRID 2221630 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:37])=[C:9]([CH2:11][O:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][O:18][C:19]3[C:23]([CH2:24][C:25]#N)=[CH:22][N:21]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:20]=3)=[CH:15][C:14]=2[O:35][CH3:36])[N:10]=1.C(O)C.[OH-:41].[Na+].Cl.[OH2:44]>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:37])=[C:9]([CH2:11][O:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][O:18][C:19]3[C:23]([CH2:24][C:25]([OH:44])=[O:41])=[CH:22][N:21]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:20]=3)=[CH:15][C:14]=2[O:35][CH3:36])[N:10]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 69216098{3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}acetonitrile

Product 1

HCID 69216430[3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-phenyl-1H-pyrazol-4-yl]acetic acidYield 91%

Procedure

To a mixture of {3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}acetonitrile (0.86 g) and ethanol (30 mL) was added 2N aqueous sodium hydroxide solution (30 mL), and the mixture was heated under reflux for 6 hrs. The reaction mixture was neutralized by adding 1N hydrochloric acid and water; and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give {3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}acetic acid as yellow crystals (0.80 g, yield 91%). Recrystallization from ethyl acetate-hexane gave yellow prism crystals. melting point: 179-180° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. extractionand the mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b0de3acbc7842f2b3a4f77196d4b3ab
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…