Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 58088350 | HCID 58088350 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58088341 | HCID 58088341 | 54% |
Reaction Steps
A mixture of 6-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-1H-indole-3-carboxylic acid methyl ester (80 mg, 0.15 mmol), 5 N sodium hydroxide (150 μL, 0.750 mmol), methanol (2 mL) and THF (1 mL) is heated at 85° C. for five hours. The mixture is cooled and 5 mL of water is added and the volatile solvents are evaporated under reduced pressure. The basic layer is washed with ether and then acidified with 1 N HCl and extracted with ether. The second ether layers are dried over anhydrous magnesium sulfate, are concentrated, and are crystallized from ether-hexane to provide 42 mg (54%) of the title compound. LC-ES/MS m/e 535.0 (M+1), 93.2% purity.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07863302B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-20df775f2d614614ae3ddaaae5c12133 |
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| Source note | uspto-grants-2011_01 |
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