Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 71294185 | HCID 71294185 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 71294264 | HCID 71294264 | — |
Reaction Steps
In THF (3 mL) was dissolved 1-(5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl) thiazol-2-yl)ethanone (356 mg, 1.05 mmol) obtained in Step 3. To the solution were added acetic acid (0.072 mL, 1.26 mmol) and tetrabutylammonium fluoride (1.0 mol/L solution in THF, 1.26 mL, 1.26 mmol) and the mixture was stirred at room temperature for 1 hour. A saturated aqueous sodium carbonate solution was added to the reaction mixture. Extraction with ethyl acetate, washing with a saturated aqueous ammonium chloride solution and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give Compound A46 (214 mg, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150569B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-afe78c7830d94132a3f257885f727f93 |
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| Source note | uspto-grants-2015_10 |
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