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 Example 1 and ethyl acetate (10 mL) were added 4-trifluoromethoxybenzoyl chloride (1.83 g) and pyridine (0.72 mL). The mixture was stirred at 60° C. for 25 hrs. Ethyl acetate (60 mL) was added to the reaction mixture, and the mixture was washed with water (30 mL), a saturated aqueous sodium hydrogen carbonate solution (20 mL) and water (20 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride—ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 14.5 hrs., the mixture was concentrated under reduced pressure. The residue was washed twice with ethyl acetate (15 mL), and dried under reduced pressure at 60° C. to give the title compound (1.83 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08980322B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-e7a4f39858ad4b4d8cda5f03f9b0e9ec |
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| Source note | uspto-grants-2015_03 |
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