Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 58755267 | HCID 58755267 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23111681 | HCID 23111681 | 66% |
Reaction Steps
To a solution of ethyl {5-[(4-{[(4-phenyl-1,3-thiazol-2-yl)(propyl)amino]methyl}benzyl)oxy]-2,3-dihydro-1H-inden-1-yl}acetate (0.684 g, 1.17 mmol) in a mixed solvent of ethanol (6 mL) and tetrahydrofuran (6 mL) was added 2 M aqueous sodium hydroxide solution (2 mL), and the mixture was stirred at room temperature for 24 hr. Water was added to the reaction mixture, and the mixture was neutralized 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 (30%-80% ethyl acetate/hexane) and recrystallized from ethyl acetate-hexane to give the title compound (0.393 g, yield 66%) as colorless prism crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820837B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-8fd1ae266cf1412ea06644bb53d1dcb1 |
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| Source note | uspto-grants-2010_10 |
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