Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-(Trifluoromethyl)benzoic acid | HCID 9963 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 66939348 | HCID 66939348 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58127830 | HCID 58127830 | 75.9% |
Reaction Steps
To a solution (16 mL) of the compound (3.0 g, 16 mmol) obtained in Example 72a in N,N-dimethylformamide were added 3-trifluoromethylbenzoic acid (3.2 g, 17 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (3.6 g, 19 mmol), 1-hydroxybenzotriazole (2.9 g, 19 mmol) and triethylamine (4.3 mL, 31 mmol), and the mixture was stirred at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (4.0 g, 66%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08461348B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-69f18bd3449845818f6278fcbb093398 |
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| Source note | uspto-grants-2013_06 |
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