Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | 4-(Trifluoromethoxy)benzoyl Chloride | HCID 142110 | — |
| Reactant | N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol | HCID 545700 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23093508 | HCID 23093508 | 82.3% |
Reaction Steps
To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.30 g) obtained in Reference Synthetic Example 1 and ethyl acetate (10 mL) were added 4-trifluoromethoxybenzoyl chloride (1.83 g) and pyridine (0.72 mL). The reaction solution was stirred at 60° C. for 25 hrs. Ethyl acetate (60 mL) was added to the reaction solution, and washed sequentially with water (30 mL), saturated aqueous solution of sodium bicarbonate (20 mL) and water (20 mL), followed by drying over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and to the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 14.5 hrs, the solution was concentrated under reduced pressure. The residue was washed twice with ethyl acetate (15 mL), and dried at 60° C. under reduced pressure to give title compound as white solid (1.83 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08449911B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-158fd8b210ca487597cde370d444ea66 |
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| Source note | uspto-grants-2013_05 |
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