Triethylamine → (S)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

HRID 403699

Reaktionsgleichung

Reaktionsgleichung von HRID 403699
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[C:18]([O:20]C)=O.Cl.[CH3:23][O:24][C:25](=[O:31])[C@H:26]([CH:28]([CH3:30])[CH3:29])[NH2:27].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:29][CH:28]([CH3:30])[C@H:26]([N:27]1[CH2:2][C:3]2[C:4](=[CH:5][C:6]([C:9]3[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=3)=[CH:7][CH:8]=2)[C:18]1=[O:20])[C:25]([O:24][CH3:23])=[O:31]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 111190Methyl valinate hydrochlorideHCID 67306641Methyl 4-(bromomethyl)-4'-nitrobiphenyl-3-carboxylate

Produkt 1

HCID 131731440(S)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of the compound of example 4 (1.54 g, 0.0044 mol) and L-valine methyl ester hydrochloride (0.813 g, 0.0048 mol) was taken in toluene (30 mL) in a round bottom flask. To this reaction mixture, triethyl amine (0.98 g, 0.0097 mol) was added and refluxed for 3-4 h. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated to obtain an oily material, which was purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether).

Aufarbeitung

  1. temperaturerefluxed for 3-4 h
  2. customAfter completion of the reaction
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain an oily material, which
  7. customwas purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-c2862bf43348472a8229bbef8caf8c2b
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748426B2

Verknüpfte Notizen

Wird geladen…