Bromoacetonitrile → (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile

HRID 503920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503920
[CH:1]([N-:4]C(C)C)(C)[CH3:2].[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[C@@H:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])=[C:12]([O:28][CH3:29])[CH:11]=1.BrCC#N.[NH4+].[Cl-]>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([C:17]([N:19]2[C@@H:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])[CH2:2][C:1]#[N:4])=[C:12]([O:28][CH3:29])[CH:11]=1

Komponenten

6

Edukt 4

HCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 66877012(S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one

Produkt 1

HCID 66877211(S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrileAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium diisopropylamide (2.0 M in heptane/THF/ethylbenzene, 1.58 mL, 3.16 mmol) was added to a solution of (S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one (1.126 g, 3.16 mmol) in THF (11 mL) under argon atmosphere at −78° C. The mixture was stirred for 15 minutes and bromoacetonitrile (0.23 mL, 3.32 mmol) was added at −78° C. The mixture was stirred for 3 hours at 0° C., and then a saturated solution of NH4Cl was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 85/15) to give 755 mg (60% yield) of (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred for 3 hours at 0° C.
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 85/15)

Quellen und Nachweise

ORD-Eintrag
ord-f802fb5a807045999ad86eadd2621f34
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776910B2

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