Triethylamine → (R)-Methyl 2-(5-bromo-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403954

Reaktionsgleichung

Reaktionsgleichung von HRID 403954
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=O)=[C:4]([CH2:12]Br)[CH:3]=1.Cl.[CH3:15][O:16][C:17](=[O:23])[C@@H:18]([CH:20]([CH3:22])[CH3:21])[NH2:19].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:8])[N:19]([C@H:18]([CH:20]([CH3:22])[CH3:21])[C:17]([O:16][CH3:15])=[O:23])[CH2:12]2

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 11984198Methyl D-valinate hydrochlorideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Produkt 1

HCID 86673568(R)-Methyl 2-(5-bromo-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 4-bromo-2-(bromomethyl)benzoate (650 mg, 2.12 mmol) and D-valine methyl ester hydrochloride (527 mg, 3.15 mmol) was taken in toluene (6.5 mL) and to this reaction mixture, triethyl amine (428 mg, 4.24 mmol) was added and refluxed for about 16 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 oil, which was purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether) to obtain the title compound.

Aufarbeitung

  1. additionwas added
  2. temperaturerefluxed for about 16 h
  3. customAfter completion of the reaction
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto obtain an oil, which
  8. customwas purified by column chromatography (silica gel, 30% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-efc7154324b44a98a9ea05ea0f974348
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748426B2

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