Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 67044040 | HCID 67044040 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 58201241 | HCID 58201241 | 54% |
Reaction Steps
A mixture of {5-fluoro-2-methyl-3-[3-(thiophene-2-sulfonyl)thiophen-2-ylmethyl]indol-1-yl}acetic acid methyl ester (0.17 g), tetrahydrofuran (0.35 mL) and water (0.35 mL) was treated with lithium hydroxide (0.088 g), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was cooled to 0° C., pH adjusted to 5 by the addition of 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC, eluting with a mixture of acetonitrile and water (3:7 to 9:1 by volume) to afford the title compound as a white solid (0.089 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394836B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-da8eb416535841e7980f1cffad6b2faf |
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| Source note | uspto-grants-2013_03 |
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