Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 86686908 | HCID 86686908 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 71604172 | HCID 71604172 | 93% |
Reaction Steps
To a solution of {4-[1-(2,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (52 mg, 0.099 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (42.4 mg, 1.0 mmol) in water (2 mL). The reaction mixture was stirred at room temperature overnight under nitrogen. After this time, the reaction mixture was diluted with water (˜20 mL) and then acidified with 1.0 N aqueous HCl (2 mL). The resulting mixture was extracted with ethyl acetate (2×25 mL), then the combined extracts were washed with brine (30 mL). The organic phase was dried over anhydrous MgSO4, filtered, and concentrated to provide {4-[1-(2,5-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (47 mg, 93%) as a yellow film. MS cald. for C24H23Cl2FNO4S [(M+H)+]: 510, obsd. 510.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08691993B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-f3ce0f24879f446ba09515062d231937 |
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| Source note | uspto-grants-2014_04 |
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