HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-[(5-methylisoxazol-3-yl)oxymethyl]oxazolidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Hymexazol | HCID 24781 | — |
| Reactant | Diisopropyl azodicarboxylate | HCID 5363146 | — |
| Reactant | 5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one | HCID 18684841 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (5R)-3-[4-(3,6-dihydro-2H-pyran-4-yl)-3-fluoro-phenyl]-5-[(5-methylisoxazol-3-yl)oxymethyl]oxazolidin-2-one | HCID 497378 | 46.1% |
Reaction Steps
5(R)-hydroxymethyl-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one (300 mg, 1.02 mmol), 3-hydroxy-5-methylisoxazole (120 mg, 1.21 mmol), triphenylphosphine (270 mg, 1.03 mmol) and diisopropylazodicarboxylate (204 mg, 1.01 mmol) were reacted in THF (8.0 ml) using the general method of Example 1. The resultant product was purified by flash chromatography (Merck 9385 silica, EtOAc/isohexane (7:3) eluant) to give the title product (176 mg, 46%) as a crystalline solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06617339B1 |
| Source dataset | uspto-grants-2003_09 |
| ORD ID | ord-9759d8846940478da0863aa0df55681e |
| Source note | uspto-grants-2003_09 |