Ethyl 2-(diphenylmethyleneamino)acetate → HCID 58222080, Verbindung

HRID 1192364Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192364
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].CC(C)([O-])C.[K+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[CH3:36]>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[CH3:36])[CH3:2]

Komponenten

6

Edukt 3

HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 23665647Potassium tert-butoxideHCID 53403081Benzene, 1-(bromomethyl)-4-chloro-2-methyl-

Produkt 1

HCID 58222080HCID 58222080, VerbindungAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution containing (Benzhydrylidene-amino)-acetic acid ethyl ester (2.3 g, 8.6 mmol) in 50 mL of DMSO under a nitrogen atmosphere was added potassium t-butoxide (1.2 g, 11 mmol) After stirring for 20 minutes, 1-Bromomethyl-4-chloro-2-methyl-benzene (1.89 g, 8.6 mmol) was added and the reaction allowed to stir at room temperature overnight. The reaction was diluted with ethyl acetate and washed with brine. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 20% ethyl acetate/hexanes gave 2-(Benzhydrylidene-amino)-3-(4-chloro-2-methyl-phenyl)-propionic acid ethyl ester (1.75 g, 50%) as a yellow oil. LCMS (APCI+) m/z 406 [M+H]+; Rt: 4.16 min.

Aufarbeitung

  1. stirringto stir at room temperature overnight
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 20% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-10027a9d26604e77b24978e6302068ff
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680114B2

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