HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N-((2S)-1-((2-(3-fluoro-4-(3-oxobutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Thiosulfate | HCID 24477 | — |
| Reactant | Triacetoxyperiodinane | HCID 159087 | — |
| Reactant | N-((2S)-1-((2-(3-fluoro-4-(3-hydroxybutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide | HCID 86731420 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-((2S)-1-((2-(3-fluoro-4-(3-oxobutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide | HCID 86731421 | 55.3% |
Reaction Steps
A solution of N-((2S)-1-((2-(3-fluoro-4-(3-hydroxybutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide (300 mg) and Dess-Martin reagent (914 mg) in DMF (30 mL) was stirred at room temperature for 15 hr. To the mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was stirred at room temperature for 10 min. Water was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer were 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 (ethyl acetate/methanol) to give the title compound (165 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133129B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-2d26735c50a143d5873dcbdfa00d81fb |
| Source note | uspto-grants-2015_09 |