Hydrochloric Acid → 2-[2-[4-[(5-Methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid
Reaction equation
[CH3:1][C:2]1[S: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:31]=[CH:30][C:18]([CH2:19][O:20][C:21]2[C:26]([CH2:27][C:28]#N)=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.COCCO.[OH-:37].[K+].Cl.[OH2:40]>>[CH3:1][C:2]1[S: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:31]=[CH:30][C:18]([CH2:19][O:20][C:21]2[C:26]([CH2:27][C:28]([OH:40])=[O:37])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1Participants
Reactant 5
Product 1
Procedure
To a mixture of 2-[2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile (0.94 g) and 2-methoxyethanol (8 mL) was added a 4N aqueous potassium hydroxide solution (4 mL) and the mixture was heated under reflux for 5 hrs. 1N Hydrochloric acid (16 mL) and water were added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (0.58 g, 59%) of 2-[2-[4-[(5-methyl-2-phenyl-4-thiazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid from a fraction eluted with acetone-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 128-129° C.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 5 hrs
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-929570305608464b91fd02110520335c
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238716B2
Reaction notes
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