Propanoyl chloride, 2-(4-bromophenyl)- → (4R,5S)-3-[2-(4-Bromo-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

HRID 553731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553731
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.C([Li])CCC.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:30])[C:27](Cl)=[O:28])=[CH:22][CH:21]=1>O1CCCC1>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([CH3:30])[C:27]([N:3]2[C@H:2]([CH3:1])[C@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[O:5][C:4]2=[O:13])=[O:28])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 569060Propanoyl chloride, 2-(4-bromophenyl)-HCID 2733812(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinoneHCID 178418339Butyllithium

Produkt 1

HCID 58539632(4R,5S)-3-[2-(4-Bromo-phenyl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone (0.348 g, 1.96 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. n-Butyllithium (1.6M in hexanes; 1.64 mL, 2.62 mmol) was added, and the reaction was stirred for 1 hour at −78° C. 2-(4-Bromo-phenyl)-propionyl chloride (0.540 g, 2.18 mmol) in tetrahydrofuran (10 mL) was added, and the reaction was stirred for 30 minutes. The mixture was concentrated, and the residue was partitioned between EtOAc and water. The organic layer was separated, dried, and concentrated, and the crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes) to give two diastereomers as separated products. Diastereomer A was the first product to come off the column, while Diastereomer B was the second product to come off the column.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred for 30 minutes
  3. concentrationThe mixture was concentrated
  4. customthe residue was partitioned between EtOAc and water
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customthe crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes)
  9. customto give two diastereomers
  10. customas separated products

Quellen und Nachweise

ORD-Eintrag
ord-d66cb5c08bcd4c96abc9bfc39151d3af
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048902B2

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