Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 58338634 | HCID 58338634 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58338638 | HCID 58338638 | 87.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08686014B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-d40f165c03ef493283c2cedd8d3f44cf |
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| Source note | uspto-grants-2014_04 |
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