(RS)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one → (R)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one

HRID 1186179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186179
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C:8]2([CH3:14])[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:7]=1>C(O)C.ClCCl.CCCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C@:8]2([CH3:14])[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:7]=1

Komponenten

3

Edukt 1

HCID 58563120(RS)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one

Produkt 1

HCID 58563016(R)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86658618Ethanol dichloromethane heptaneLösungsmittel

Versuchsvorschrift

A solution of the (RS)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one (20.2 g) in ethanol/dichloromethane/heptane (4/2/2) was divided in 1 g aliquots which were separated on chiral HPLC (Chiralpak AD) using a 90:10-mixture of ethanol and heptane as the eluent. The first eluting enantiomer (retention time: 7.98 min), the (R)-(−)-4-(5-bromo-2-fluoro-phenyl)-4-methyl-oxazolidin-2-one (intermediate C5A), was obtained as a brownish crystalline solid (9.154 g, 45.3% of theory), and the second eluting enantiomer (retention time: 12.19 min), the (S)-(+)-N-[1-(5-bromo-2-fluoro-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide, was also obtained as a light brown crystalline solid (9.25 g, 45.8% of theory), with e.e. >99.5% each.

Aufarbeitung

  1. customwere separated on chiral HPLC (Chiralpak AD)

Quellen und Nachweise

ORD-Eintrag
ord-dca1e22a71a64178a039592205be3c69
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673894B2

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