Reaction #56711

Reaction equation

oxazolidinone

n-butyllithium

oxalyl chloride

(R)-4-methyl-octanoic acid

CH2Cl2

→

titled compound

(4R, 5S)-4-Methyl-3-((R)-4-methyl-octanoyl)-5-phenyl-oxazolidin-2-one

Solvents

THF

—

hexanes

THF

Conditions

Workup

1. 1
   Otherresulting in vigorous gas evolution
2. 2
   Concentrationconcentrated
3. 3
   workup.ADDITIONwas added dropwise
4. 4
   workup.STIRRINGThe reaction was stirred 30 minutes at −78° C.
5. 5
   Temperaturewarmed directly to ambient temperature
6. 6
   Otherquenched with sat. NH4Cl
7. 7
   OtherThe mixture was partitioned between Et2O and sat. NH4Cl (aq)
8. 8
   Otherthe phases were separated
9. 9
   Dryingthe organic phase dried (MgSO4)
10. 10
    Concentrationconcentrated

Procedure

To (R)-4-methyl-octanoic acid (2.14 g, 13.5 mmol) in 25 mL CH2Cl2 at 0° C. was added 3 drops DMF, followed by oxalyl chloride (1.42 mL, 16.2 mmol) resulting in vigorous gas evolution. The solution was warmed directly to ambient temperature, stirred 30 minutes, and concentrated. Meanwhile, to a solution of the oxazolidinone (2.64 g, 14.9 mmol) in 40 mL THF at −78° C. was added n-butyllithium (1.6 M soln in hexanes, 9.3 mL, 14.9 mmol) dropwise. The mixture was stirred for 10 minutes at which time the acid chloride in 10 mL THF was added dropwise. The reaction was stirred 30 minutes at −78° C., then warmed directly to ambient temperature and quenched with sat. NH4Cl. The mixture was partitioned between Et2O and sat. NH4Cl (aq), the phases were separated, and the organic phase dried (MgSO4), and concentrated to furnish 3.2 g of the titled compound as a colorless oil. LRMS: m/z 318.2 (M+).

Source