Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol | HCID 545700 | — |
| Reactant | 3,4-Difluorobenzoyl chloride | HCID 2724519 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23093457 | HCID 23093457 | 81.6% |
Reaction Steps
To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic Example 1 and ethyl acetate (10 mL) were added 3,4-difluorobenzoyl chloride (1.77 g) and pyridine (0.97 mL). After stirring at room temperature for 3 days, ethyl acetate (80 mL) was added to the reaction solution, and washed sequentially with water (20 mL), saturated aqueous solution of sodium bicarbonate (20 mL) and water (20 mL), and dried 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 4 hrs, the solution was concentrated under reduced pressure. The residue was washed with ethyl acetate (15 mL), and dried at 60° C. under reduced pressure to give title compound as white solid (2.05 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-ce402ec74f254174ad02ae0db916b42f |
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| Source note | uspto-grants-2013_05 |
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