HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → HCID 67173612, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Oxazolidinone | HCID 73949 | — |
| Reactant | L-Proline | HCID 145742 | — |
| Reactant | Ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate | HCID 58297650 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67173612 | HCID 67173612 | 10% |
Reaction Steps
To a mixture of ethyl 7-(4-bromophenyl)-4,7-dioxoheptanoate ((36A, where Ar1-Br=4-bromophenyl, also see compound 5B, Scheme 5) (1.50 g, 4.4 mmol) and oxazolidin-2-one (575 mg, 6.6 mmol) in dioxane (5 mL) were added L-proline (50 mg, 0.44 mmol), CuI (42 mg, 0.22 mmol) and K2CO3 (1.22 g, 8.8 mmol). The resultant mixture was stirred under N2 at 110° C. for 48 h and then evaporated. The residue was diluted with EA/water (40 mL/40 mL). The mixture was filtered and the resultant aqueous layer was extracted with EA (30 mL×5). The combined organic layers were washed with brine, dried over NaSO4, concentrated and purified by silica gel column chromatography (pure DCM to DCM:MeOH=30:1) to afford titled compound as a white solid (158 mg, yield 10%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08691816B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-b84fe24db3254451bfba8d9a8475420c |
| Source note | uspto-grants-2014_04 |