Benzyl Bromide → Benzyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

HRID 420642

Reaktionsgleichung

Reaktionsgleichung von HRID 420642
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH2:3][C:4]([O-:6])=[O:5].[Li+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=1)[CH2:3][C:4]([O:6][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:5]

Komponenten

6

Edukt 2

HCID 7498Benzyl BromideHCID 23693664Lithium 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

Produkt 1

HCID 59666221Benzyl 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of lithium 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate (2.0 g, 7.9 mmol) (Example 2A) in water (15 ml) is added a solution of Aliquat 336® (3.1 g) and benzyl bromide (1.35 g, 7.5 mmol) in dichloromethane (15 ml). The reaction mixture is stirred for two days at room temperature, then extracted with dichloromethane (500 ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography over silica gel 60 with cyclohexane/ethyl acetate mixtures as eluent.

Aufarbeitung

  1. extractionextracted with dichloromethane (500 ml)
  2. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography over silica gel 60 with cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-668855b86b7c461f877532ce50aa3ef7
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097629B2

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