HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 4-(4-Bromophenyl)-3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)azetidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Bistrimethylsilylacetamid | HCID 11708267 | — |
| Reactant | Tributylammonium fluoride trihydrate | HCID 22252057 | — |
| Reactant | 3-[2-[(4-Bromophenyl)-(4-fluorophenylamino)methyl]-5-(tert-butyl-dimethylsilanyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyloxazolidin-2-one | HCID 22252067 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Product | 4-(4-Bromophenyl)-3-[3-(tert-butyldimethylsilanyloxy)-3-(4-fluorophenyl)propyl]-1-(4-fluorophenyl)azetidin-2-one | HCID 22252077 | — |
Reaction Steps
3.34 g of 3-[2-[(4-bromophenyl)-(4-fluorophenylamino)methyl]-5-(tert-butyl-dimethylsilanyloxy)-5-(4-fluorophenyl)pentanoyl]-4-phenyloxazolidin-2-one are suspended in 70 ml of tert-butyl methyl ether. 3.8 ml of bis(trimethylsilyl)acetamide and 144 mg of tributylammonium fluoride trihydrate are then added. The reaction mixture is stirred at room temperature overnight, and 0.7 ml of glacial acetic acid are then added. The reaction mixture is concentrated using a rotary evaporator and the residue is purified by column chromatography (SiO2; ethyl acetate/heptane 1:4). The product is obtained as a clear oil. C30H34BrF2NO2Si (586) MS (ESI): M+-131
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07488829B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-54f1689641834cd5893d4869c9435648 |
| Source note | uspto-grants-2009_02 |