Hydrochloric Acid → 2-[2-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]acetic acid
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[C:27]([CH2:28][C:29]#N)=[CH:26][CH:25]=[CH:24][N:23]=2)[O:17][N:16]=1.[OH-:31].[Na+].C(O)C.Cl.[OH2:37]>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[C:27]([CH2:28][C:29]([OH:37])=[O:31])=[CH:26][CH:25]=[CH:24][N:23]=2)[O:17][N:16]=1Participants
6
Reactant 5
Product 1
Procedure
A mixture of 2-[2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]acetonitrile (1.02 g), a 2N aqueous sodium hydroxide solution (10 mL) and ethanol (20 mL) was heated under reflux for 5 hrs. Water was added to the reaction mixture, and the mixture was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give crystals (820 mg, 77%) of 2-[2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]-3-pyridyl]acetic acid. Recrystallization from ethyl acetate-isopropyl ether gave colorless needle crystals. melting point: 129-130° C.
Workup
- temperatureunder reflux for 5 hrs
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0061a7def0da4919965cc2cce1fcf017
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238716B2
Reaction notes
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