HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate | HCID 117759876 | — |
| Reactant | 2'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl trifluoromethanesulfonate | HCID 117760123 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-yl)oxy)methyl)phenyl)propanoate | HCID 117759787 | 80.8% |
Reaction Steps
To a solution of 2′-fluoro-4-hydroxy-5′-methoxybiphenyl-2-yl trifluoromethanesulfonate (1.30 g) in THF (30 mL) were added ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (1.02 g), triphenylphosphine (1.87 g) and a 40% solution of diethyl azodicarboxylate in toluene (3.2 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.71 g) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382188B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-7a2e9ec96d5f4e519d635f2eeb870400 |
| Source note | uspto-grants-2016_07 |