HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 1-{2-[4-(4-Ethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-3,3-dimethyl-azetidin-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Chloro-2,2-dimethylpropanoyl chloride | HCID 61345 | — |
| Reactant | 1-(4-((4-Ethoxyphenyl)ethynyl)phenyl)propan-2-amine | HCID 66610433 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-{2-[4-(4-Ethoxy-phenylethynyl)-phenyl]-1-methyl-ethyl}-3,3-dimethyl-azetidin-2-one | HCID 66614078 | — |
Reaction Steps
To 33.5 mg (120 μmol) 2-[4-(4-ethoxy-phenylethynyl)-phenyl]-1-methyl-ethylamine (I64) in 2.0 mL ACN are added 166 mg (1.20 mmol) K2CO3, a few crystals DMAP and finally 23.5 μL (0.18 mmol) 3-chloropivaloyl chloride (in 1.0 mL ACN). The reaction mixture is stirred at reflux for 6 h. The solvent is removed in vacuo and the residue is resolved EtOAc and washed with water (1×), sat. aq. NaHCO3 solution (2×) and again with water. The organic layer is dried with Na2SO4 and the solvent is evaporated in vacuo. The residue is purified by HPLC (MeOH/H2O/TFA).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08835472B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-dac9277838f3451d989cfe6aa0abe744 |
| Source note | uspto-grants-2014_09 |