2-Oxazolidinone → HCID 10491506, compound

HRID 1741268Notes

Reaction equation

HRID 1741268 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([Li])[CH2:15][CH2:16]C.[O:19]1[CH2:23][CH2:22]NC1=O>C1COCC1>[O:19]=[C:23]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])[CH2:22][CH2:16][CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 739492-OxazolidinoneHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10491506HCID 10491506, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

In a separate flask, a solution of 17.7 g (100 mmol) of (S)-4-benzyl-2-oxazolidinone in 120 mL of THF was cooled to -78° C. whereupon 63.1 mL (101 mmol) of 1.6 M n-butyllithium in hexanes was added slowly. This solution was stirred for 10 min at -78° C. The flask containing the mixed anhydride was cooled to -78° C. and the lithiated oxazolidinone was cannulated into the mixed anhydride. After stirring at -78° C. for 15 min, the reaction mixture was warmed to 0° C. and stirred for 30 min. After quenching with water, the layers were separated and the aqueous layer was washed with ether. The combined organic layers were washed with brine, dried, filtered and concentrated. The residue was purified by filtration through a pad of silica gel (3:1 hexanes: ethyl acetate) to give 25.88 g (100%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 2.42 (m,2H); 2.72 (dd, J=9.7, 13 Hz, 1H); 3.03 (m, 2H; 3.29 (dd, J=13, 4 Hz, 1H); 4.15 (m, 2H); 4.65 (m,1H); 5.07 (m,2H); 5.86 (m, 1H); 7.12-7.37 (m, 5H). 13C NMR (CDCl3) δ 28.17, 34.78, 37.9, 55.14, 66.2, 115.7, 127.3, 128.9, 129.4, 135.2, 136.7, 153.4, 172.5. IR (film) 1790, 1708, 1390 cm-1 [α]24D+64.22° (c=0.83, CHCl3) Anal: Calcd. for C15H17O3N: C, 69.48; H, 6.61; N, 5.40. Found: C, 69.20; H, 6.65; N, 5.33.

Workup

  1. additionwas added slowly
  2. temperaturewas cooled to -78° C.
  3. stirringAfter stirring at -78° C. for 15 min
  4. temperaturethe reaction mixture was warmed to 0° C.
  5. stirringstirred for 30 min
  6. customAfter quenching with water
  7. customthe layers were separated
  8. washthe aqueous layer was washed with ether
  9. washThe combined organic layers were washed with brine
  10. customdried
  11. filtrationfiltered
  12. concentrationconcentrated
  13. filtrationThe residue was purified by filtration through a pad of silica gel (3:1 hexanes: ethyl acetate)

Sources & evidence

ORD record
ord-de19f816d90f4a13bb1914d19c678d66
Source dataset
uspto-grants-1999_10
Patent number
US05973161

Reaction notes

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