Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 67454366 | HCID 67454366 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | HCID 67458520 | HCID 67458520 | 64.3% |
Reaction Steps
Under an argon atmosphere, a free base of Compound 48 (57 mg, 0.14 mmol) obtained in Example 48 was dissolved in trifluoroacetic acid (1 mL), and triethylsilane (91 μL, 0.57 mmol) was added thereto, and then, the mixture was stirred overnight at room temperature. Under ice-cooling, an aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20) to give a free base of the title compound (35 mg, 0.09 mmol, yield: 64%). Then, the obtained free base was treated with 4 mol/L hydrogen chloride-ethyl acetate to give the title compound 51 (30 mg, 0.07 mmol, yield: 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08273738B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-30314ea611ca4603a422810a1487ef9f |
|---|
| Source note | uspto-grants-2012_09 |
|---|