HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 57504574, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Tetrabutylammonium Fluoride Trihydrate | HCID 11726816 | — |
| Reactant | HCID 57504576 | HCID 57504576 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 57504574 | HCID 57504574 | 52.7% |
Reaction Steps
Tetrabutylammoniumfluoride trihydrate (417 mg, 1.32 mmol) was added to a stirred solution of (2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-(dimethylamino)-N-(5-methylpyridin-2-yl)butanamide (Step 3) (310 mg, 0.88 mmol) in THF (5 mL). The reaction mixture was kept at ambient temperature for 30 minutes. Water and EtOAc were added and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:10/1) to give the title compound as a solid (110 mg), 1H NMR (300 MHz, CDCl3) δ 9.44 (br s, 1H), 8.15 (d, 1H), 8.12 (d, 1H), 7.51 (dd, 1H), 4.39 (dd, 1H), 2.63 (m, 2H), 2.28 (m, 9H), 2.09 (m, 1H), 1.92 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08143263B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-d581c441b7fa456f9598f24ceffddddd |
| Source note | uspto-grants-2012_03 |