Reaktionsgleichung
[CH3:1][C@H:2]1[C@@H:10]2[C:6](=[C:7]([CH3:11])[CH2:8][CH2:9]2)[C@H:5](/[CH:12]=[C:13](/[C:15]([OH:17])=[O:16])\[CH3:14])[CH2:4][CH2:3]1.C([N:20](CC)CC)C.ClC(OC)=O.N>C1COCC1>[CH3:1][C@H:2]1[C@@H:10]2[C:6](=[C:7]([CH3:11])[CH2:8][CH2:9]2)[C@H:5](/[CH:12]=[C:13](/[C:15]([OH:17])=[O:16])\[CH3:14])[CH2:4][CH2:3]1.[CH3:1][C@H:2]1[C@@H:10]2[C:6](=[C:7]([CH3:11])[CH2:8][CH2:9]2)[C@H:5](/[CH:12]=[C:13](/[C:15]([NH2:20])=[O:17])\[CH3:14])[CH2:4][CH2:3]1Komponenten
7
Edukt 4
Produkt 2
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Valerenic acid (18.9 mg, 0.0807 mmol) was dissolved in THF (3 mL) and cooled to 0° C. Triethylamin (12.0 μL, 8.76 mg, 0.0866 mmol) and methyl chloroformate (97%, 8.5 μL, 9.36 mg, 0.0862 mmol) were added. After stirring for 1 hour the resulting solution was treated with aqueous ammonia (25% 25 μL, 5.5 mg, 0.3230 mmol). After 30 minutes the reaction mixture was warmed to room temperature and stirred for an additional hour. Then the mixture was filtrated and the filtrate concentrated in vacuo. Purification by chromatography (pure diethylether to diethylether/EtOAc 1/1) provided 6.6 mg Valerenic acid and 11.2 mg of Valerenic acid amide as white solid with 92% yield based on recovered starting material.
Aufarbeitung
- temperatureAfter 30 minutes the reaction mixture was warmed to room temperature
- stirringstirred for an additional hour
- filtrationThen the mixture was filtrated
- concentrationthe filtrate concentrated in vacuo
- customPurification by chromatography (pure diethylether to diethylether/EtOAc 1/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-f330f0febe7b45ef92818f4f1a40913a
- Quelldatensatz
- uspto-grants-2014_08
- Patentnummer
- US08809395B2
Verknüpfte Notizen
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