Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 67458316 | HCID 67458316 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 25095814 | HCID 25095814 | 64.5% |
Reaction Steps
A solution of [4-difluoromethoxy-3-(4-ethanesulfonylaminobenzyl)-2-ethyl-8-fluoroquinolin-5-yloxy]acetic acid methyl ester (0.051 g) in methanol (5.0 mL) and water (0.5 mL) was treated with 5.0 M aqueous sodium hydroxide solution (0.25 mL), and the resulting mixture was left to stand at room temperature for 1 hour. The mixture was acidified by the addition of glacial acetic acid, concentrated under reduced pressure, and the residue partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate, and then concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane, methanol and glacial acetic acid (100:1:0.5 to 25:1:0.125 by volume) gave title compound as a cream solid (0.032 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08173812B2 |
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| Source dataset | uspto-grants-2012_05 |
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| ORD ID | ord-4474b0ed1f4e40afb3ea108a5ebc24a4 |
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| Source note | uspto-grants-2012_05 |
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