HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-2-methyl-propionic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Propanoic acid, 2-bromo-2-methyl-, ethyl ester | HCID 11745 | — |
| Reactant | 1-Cyclohexyl-3-(3,5-dichloro-4'-hydroxy-biphenyl-4-ylmethyl)-pyrrolidin-2-one | HCID 59299335 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-[3',5'-Dichloro-4'-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-4-yloxy]-2-methyl-propionic acid ethyl ester | HCID 11606223 | 104.3% |
Reaction Steps
Combine 1-Cyclohexyl-3-(3,5-dichloro-4′-hydroxy-biphenyl-4-ylmethyl)-pyrrolidin-2-one (prep 55) (0.15 g, 0.36 mmol), ethyl 2-bromoisobutyrate (0.28 g, 1.43 mmol) and Cs2CO3 (0.35 g, 1.07 mmol) in DMF (7 mL) and heat to 60° C. for 16 hours. Cool the reaction, extract with diethyl ether and water, dry (Na2SO4) and then purify by normal phase chromatography (30 to 80% gradient of ethyl acetate in hexanes) to afford 200 mg (100%) of the title compound: LC-MS (ES +) m/z=exact mass calcd for C29H35Cl2NO4 531, found 532 and 534 (M+1 and M+3, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07713979B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-8c7aa6d982004f33b64288b9ff6ab86c |
| Source note | uspto-grants-2010_05 |