Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Triphenylphosphine | HCID 11776 | — |
| Edukt | Diethyl azodicarboxylate | HCID 5462977 | — |
| Edukt | (2-Methylquinolin-4-yl)methanol | HCID 10149033 | — |
| Edukt | 5-(4-hydroxy-phenylsulfanyl methyl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester | HCID 71195099 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | HCID 69432329 | HCID 69432329 | 8% |
Reaktionsschritte
To a solution of DEAD (81 mg, 0.46 mmol) in 3 mL of THF at 0° C. was added PPh3 (120 mg, 0.46 mmol). After dissolution of PPh3, 4d (100 mg, 0.31 mmol) was added and the solution was stirred for 15 min. (2-methyl-4-quinolinyl)methanol was then added as a solid. After stirring for 2 h, 3 mL of DMF was added to aid dissolution. The mixture was stirred at room temperature overnight before it was quenched with water. The solution was extracted with CH2Cl2 and the organic layer was dried over MgSO4. After filtration and concentration, the residue was purified by flash column chromatography to provide 5-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylsulfanylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester 4e (11 mg, 8%). MS (ESI+) (M+1)=436.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07211671B2 |
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| Quelldatensatz | uspto-grants-2007_05 |
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| ORD ID | ord-f3ab5768211b4e6a88490fda4322a720 |
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| Quellennotiz | uspto-grants-2007_05 |
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