Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Propanoic acid, 2-bromo-2-methyl-, ethyl ester | HCID 11745 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | HCID 57719312 | HCID 57719312 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57719306 | HCID 57719306 | 72.1% |
Reaction Steps
A mixture of 4-[3-(4-hydroxy-phenyl)-propyl]-1-(4-methyl-benzyl)-3-propyl-imidazolidin-2-one (0.687 g, 1.87 mmol), ethyl 2-bromoisobutyrate (2.55 g, 13.1 mmol), MgSO4 (0.22 g, 1.83 mmol) and 325 mesh K2CO3 (0.77 g, 5.57 mmol) in ethanol (60 mL) was heated at 70° C. for under N2 for 16 h. The reaction mixture was cooled and the solvent removed in vacuo to give a residue that was acidified with 1 N HCl (20 mL). The reaction was diluted with EtOAc and washed with water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 5:1 hexanes:acetone to afford 0.648 g (72%) 2-methyl-2-(4-{3-[1-(4-methyl-benzyl)-2-oxo-3-propyl-imidazolidin-4-yl]-propyl}-phenoxy)-propionic acid ethyl ester. MS (ES+) Calc'd for C29H41N2O4 (M+1) 481. Found m/z 481 (100%). 1H NMR.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07544812B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-4981615bd04e4bcca4c92369b31345fd |
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| Source note | uspto-grants-2009_06 |
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