(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 1186179Notes

Reaction equation

HRID 1186179 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 86658618Ethanol dichloromethane heptaneSolvent

Procedure

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.

Workup

  1. customwere separated on chiral HPLC (Chiralpak AD)

Sources & evidence

ORD record
ord-dca1e22a71a64178a039592205be3c69
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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