Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | 4'-Hydroxyacetophenone | HCID 7469 | — |
| Edukt | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Edukt | 2-Dimethylaminopyridine | HCID 21885 | — |
| Edukt | (R)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidine-4-carboxylic acid | HCID 6932185 | — |
| Lösungsmittel | Ethyl Acetate | HCID 8857 | — |
| Produkt | HCID 69081870 | HCID 69081870 | 63,4% |
Reaktionsschritte
At 0° C., 3-tert-butoxycarbonyl-2,2-dimethyloxazolidine-4-(R)-carboxylic acid (1.0 g) is dissolved in ethyl acetate (25 ml), dicyclohexylcarbodiimide (DCC; 1.26 g) is then added and the reaction mixture is subjected to agitation for 45 minutes at 0° C. Dimethylaminopyridine (DMAP; 100 mg) and 4′-hydroxyacetophenone (565 mg) are successively added, the reaction mixture is then left to return to room temperature. After 5 hours of agitation, the mixture is filtered and the filtrate is washed with a sodium hydrogen carbonate saturated solution, then with a sodium chloride saturated solution. The organic phase is dried on MgSO4, filtered and concentrated. The obtained orange oil is purified by chromatography on silica to obtain the desired product as a transparent oil (940 mg).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07488755B2 |
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| Quelldatensatz | uspto-grants-2009_02 |
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| ORD ID | ord-f7a900afe54647e698a35ba0b75d4dfd |
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| Quellennotiz | uspto-grants-2009_02 |
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