Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 23143253 | HCID 23143253 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 11295855 | HCID 11295855 | 88% |
Reaction Steps
To a solution of ethyl 3-{2-fluoro-4-[(4-{1-[(4-phenyl-1,3-thiazol-2-yl)sulfonyl]butyl}benzyl)oxy]phenyl}propanoate (0.360 g, 0.619 mmol) in a mixture of ethanol (1.5 mL) and tetrahydrofuran (3 mL) was added 1N aqueous sodium hydroxide solution (0.75 mL), and the mixture was stirred at 50° C. for 1.5 hr. Water was added to the reaction mixture, and the mixture was weak acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-80:20) and recrystallized from ethyl acetate-hexane to give the title compound (0.300 g, yield 88%) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07585880B2 |
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| Source dataset | uspto-grants-2009_09 |
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| ORD ID | ord-3536623ffd154d6b8a7241f563494cb9 |
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| Source note | uspto-grants-2009_09 |
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