Reaktionsgleichung
[C:1]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([O-:5])=O.CN1CCOCC1.P(Cl)(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[F:39][C:40]([F:49])([F:48])[C:41]1[CH:42]=[C:43]([NH2:47])[CH:44]=[CH:45][CH:46]=1>C1COCC1>[CH2:8]([O:7][C:1](=[O:6])[CH2:2][C:3]([NH:47][C:43]1[CH:44]=[CH:45][CH:46]=[C:41]([C:40]([F:39])([F:48])[F:49])[CH:42]=1)=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Komponenten
Versuchsvorschrift
mono-Benzyl malonate (10 g) was dissolved in THF (100 ml), 4-methylmorpholine and cooled to −22° C. prior to the slow addition of diphenyl chlorophosphate (14 ml) and 3-trifluoromethyl-phenylamine (19 ml). After the reaction was warmed to rt overnight, it was heated to gently reflux for 0.5 h. After the reaction was cooled to rt, the solid was filtered off. The filtrate was concentrated. EtOAc was added along with 1N HCl solution. The organic layer was washed with NaHCO3 solution (aq) and brine, dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave N-(3-trifluoromethyl-phenyl)-malonamic acid benzyl ester (8.0 g): 1H NMR (CDCl3, δppm, 300 mHz) 3.56 (s, 2H), 5.26 (s, 2H), 7.40 (m, 7H), 7.75 (d, 1H), 7.83 (s, 1H), 9.43 (s, br, 1H).
Aufarbeitung
- temperatureit was heated
- temperatureto gently reflux for 0.5 h
- temperatureAfter the reaction was cooled to rt
- filtrationthe solid was filtered off
- concentrationThe filtrate was concentrated
- additionEtOAc was added along with 1N HCl solution
- washThe organic layer was washed with NaHCO3 solution (aq) and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-05e0347d29644926bfb2ad1dffe84085
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07696205B2
Verknüpfte Notizen
Wird geladen…