Hydrochloric Acid → HCID 58338638, compound
Reaction equation
C[O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[Br:15])[C:8]([C:16]2[CH2:20][C:19]([C:25]3[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[CH:26]=3)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=2)=[CH:7][CH:6]=1)=[O:4].[OH-].[K+].Cl>O1CCCC1.CO.O>[Br:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=[C:8]2[C:16]1[CH2:20][C:19]([C:25]2[CH:26]=[C:27]([Cl:32])[CH:28]=[C:29]([Cl:31])[CH:30]=2)([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=1Participants
Procedure
To a solution of 8-bromo-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid methyl ester (Example 8.1) (400 mg) in tetrahydrofuran (3.5 ml) was added a solution of potassium hydroxide (1.9 g) in methanol (3.5 ml) and water (3.5 ml). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was then acidified by addition of aqueous hydrochloric acid (4N) and the mixture extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with water (3×10 ml) and brine, dried over sodium sulfate and concentrated to give 8-bromo-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic acid (342 mg). LC-MS: RT=2.41 min, [M−H]−=532/534, Method A.
Workup
- extractionthe mixture extracted with ethyl acetate (3×10 ml)
- washThe combined organic extracts were washed with water (3×10 ml) and brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d40f165c03ef493283c2cedd8d3f44cf
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08686014B2
Reaction notes
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