Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bromoacetyl bromide | HCID 61147 | — |
| Reactant | HCID 23144459 | HCID 23144459 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23144481 | HCID 23144481 | 69.1% |
Reaction Steps
Compound 286 (150 mg, 0.526 mmol) and triethylamine (0.367 mL, 2.63 mmol) were dissolved in THF (4 mL), and bromoacetyl bromide (0.206 mL 2.37 mmol) was added thereto at 0° C., followed by stirring for 1 hour at room temperature. Further, a solution (2 mL) of morpholine (0.689 mL, 7.89 mmol) and triethylamine (1.10 mL, 7.89 mmol) in THF was added thereto at 0° C., followed by stirring for 1 hour at room temperature. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography to afford the entitled Compound 287 (150 mg, 69%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07880013B2 |
|---|
| Source dataset | uspto-grants-2011_02 |
|---|
| ORD ID | ord-ee1bb37d5f5d448e80872c1277a42374 |
|---|
| Source note | uspto-grants-2011_02 |
|---|