Reaktionsgleichung
Cl.C(N=C=NCCCN(C)C)C.C1([NH2+]C2CCCCC2)CCCCC1.[C:26]([NH:33][C@H:34]([C:38]([O-:40])=O)[CH2:35][CH2:36][CH3:37])([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].Cl.[CH3:42][NH:43][O:44][CH3:45].O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH3:42][N:43]([O:44][CH3:45])[C:38](=[O:40])[C@H:34]([CH2:35][CH2:36][CH3:37])[NH:33][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (443 mg) in one portion was added to a mixture of N-Boc-L-norvaline dicyclohexylammonium salt (838 mg), N,O-dimethylhydroxylamine hydrochloride (215 mg), 1-hydroxybenzotriazole monohydrate (340 mg), and N-methylmorpholine (0.28 ml) in dimethyl formamide (DMF, 20 ml) at 0° C. The mixture was stirred at 0° C. for 2 hours, then at room temperature for 40 hours. The reaction was quenched with water (80 mL) and the mixture was extracted with ethyl acetate (EtOAc, 3×100 mL). The combined organic layers were washed with aqueous 10% hydrogen chloride (HCl), saturated sodium bicarbonate (NaHCO3), and brine, then dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated to afford the product (546 mg) as an oil.
Aufarbeitung
- waitat room temperature for 40 hours
- customThe reaction was quenched with water (80 mL)
- extractionthe mixture was extracted with ethyl acetate (EtOAc, 3×100 mL)
- washThe combined organic layers were washed with aqueous 10% hydrogen chloride (HCl), saturated sodium bicarbonate (NaHCO3), and brine
- dry with materialdried over anhydrous magnesium sulfate (MgSO4)
- filtrationfiltered
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-8c0bdf35f724418eb0deac8ada8c2e76
- Quelldatensatz
- uspto-grants-2003_12
- Patentnummer
- US06660268B1
Verknüpfte Notizen
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