Hydrochloric Acid → 2-[2-[3-Methoxy-4-[(2-phenyl-5-methyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[N:23]=[C:24](C2C=CC=CC=2)[O:25][C:26]=1[CH3:27])[CH2:6][O:7][C:8]1[C:13]([CH2:14][C:15]#N)=[CH:12][CH:11]=[CH:10][N:9]=1.[CH2:34](O)[CH3:35].[OH-:37].[K+].Cl.[OH2:40]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[N:23]=[C:24]([C:35]2[CH:34]=[CH:18][CH:19]=[CH:3][CH:4]=2)[O:25][C:26]=1[CH3:27])[CH2:6][O:7][C:8]1[C:13]([CH2:14][C:15]([OH:40])=[O:37])=[CH:12][CH:11]=[CH:10][N:9]=1Participants
6
Reactant 5
Product 1
Procedure
A mixture of 2-[2-[3-methoxy-4-[(2-phenyl-5-methyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile (350 mg), ethanol (5 mL) and a 4N aqueous potassium hydroxide solution (5 mL) was heated under reflux for 4 hrs. Water was added to the reaction mixture, and the reaction mixture was neutralized with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals (236 mg, 65%) of 2-[2-[3-methoxy-4-[(2-phenyl-5-methyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid. The crystals were recrystallized from ethyl acetate-hexane to give colorless prism crystals. melting point: 145-146° C.
Workup
- temperatureunder reflux for 4 hrs
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bb84c76256d84268bf9579a1c3544f47
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238716B2
Reaction notes
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