Hexanoyl chloride → HCID 10612452, compound

HRID 1396858Notes

Reaction equation

HRID 1396858 reaction equation
[C:1]1([CH2:7][C@H:8]2[CH2:12][O:11][C:10](=[O:13])[NH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:19](Cl)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[C:19]([N:9]1[C@@H:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][O:11][C:10]1=[O:13])(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 67340Hexanoyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10612452HCID 10612452, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 3000 mL RB flask was added (4S)-4-(phenylmethyl)-1,3-oxazolidin-2-one (100 g, 0.564 mol) in THF (1500 mL). The solution was cooled to −78° C. and n-butyl lithium (1.6 M in hexanes, 387 mL, 0.62 mol) was added dropwise. Stirring continued for 30 min. Hexanoyl chloride (74.8 g, 0.62 mol) was then added dropwise and the reaction was monitored by TLC. The reaction was quenched by addition of NH4Cl (400 mL), and extracted with DCM (2×500 mL). The product was purified by flash column eluting with ethyl acetate/petroleum ether (1:50 to 1:20) to afford the title compound (118 g, 76%). LCMS: (M+H)+: 276.1.

Workup

  1. customThe reaction was quenched by addition of NH4Cl (400 mL)
  2. extractionextracted with DCM (2×500 mL)
  3. customThe product was purified by flash column
  4. washeluting with ethyl acetate/petroleum ether (1:50 to 1:20)

Sources & evidence

ORD record
ord-3b4c48c202bd4e66a7a83a04e49c0061
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

Loading…