Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 91103747 | HCID 91103747 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 91072451 | HCID 91072451 | 81.7% |
Reaction Steps
tert-Butyl (rac.)-(3R,4R)-3-[({4-[2-(dibenzylamino)ethyl]-7-fluoro-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl}carbonyl)(ethyl)amino]-4-(3-hydroxyphenyl)piperidine-1-carboxylate (82.5 mg) was dissolved in acetonitrile (2 ml), and thereto were added potassium carbonate (29.8 mg) and methyl iodide (13.4 μl), and the mixture was refluxed for 3 hours. The reaction solution was cooled, and thereto was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/ethyl acetate=2/1) to give the title compound (68.6 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08389511B2 |
|---|
| Source dataset | uspto-grants-2013_03 |
|---|
| ORD ID | ord-781f80d6b68b4fcfba4dd8598c605420 |
|---|
| Source note | uspto-grants-2013_03 |
|---|