HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → [[3',5-Dichloro-4'-(1-pyrrolidinylcarbonyl)[1,1'-biphenyl]-2-yl]oxy]-acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | tert-Butyl bromoacetate | HCID 79177 | — |
| Reactant | HCID 67277611 | HCID 67277611 | — |
| Solvent | Water | HCID 962 | — |
| Product | [[3',5-Dichloro-4'-(1-pyrrolidinylcarbonyl)[1,1'-biphenyl]-2-yl]oxy]-acetic acid | HCID 11538448 | — |
Reaction Steps
The product from step c) (180 mg), tert-butyl bromoacetate (0.07 ml), potassium carbonate (0.1 g) and DMF (10 ml) were charged to a flask and stirred for 16 h. Water was added and then washed with ethyl acetate. The organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography eluting with isohexane:ethyl acetate (8:2). The sub-title compound was dissolved in DCM (8 ml) and TFA (2 ml) was added, stirred for 1 h, then concentrated in vacuo. Trituration with a mixture of ether and isohexane gave a solid, which was further purified by reverse phase HPLC to give the title compound. Yield (48 mg)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07737135B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-77362c6764ac4e2fb0ace2edf1e7fcf2 |
| Source note | uspto-grants-2010_06 |