HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Ethyl 3-(3-(((2-(2-cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)-3-cyclopropylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate | HCID 117759876 | — |
| Reactant | 3-(2'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl)-2,2-dimethylpropanenitrile | HCID 117760136 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Ethyl 3-(3-(((2-(2-cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)-3-cyclopropylpropanoate | HCID 117759562 | 84.4% |
Reaction Steps
To a solution of 3-(2′-fluoro-4-hydroxy-5′-methoxybiphenyl-2-yl)-2,2-dimethylpropanenitrile (136 mg), ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (136 mg) and tributylphosphine (0.22 mL) in toluene (5.0 mL) was added 1,1′-(azodicarbonyl)dipiperidine (225 mg), 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 (203 mg) 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-87296c1b6aa84989981ba95ca63b397d |
| Source note | uspto-grants-2016_07 |