Pyridine → HCID 18989310, compound

HRID 2395813Notes

Reaction equation

HRID 2395813 reaction equation
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[S:22]([NH:25][N:26]1[CH:30]([CH2:31][CH2:32][C:33](O)=[O:34])[C:29](=[O:36])[O:28][CH2:27]1)(=[O:24])=[O:23].N1C=CC=CC=1.[H-].C(O[Al](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+]>C(Cl)Cl.C1COCC1>[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[S:22]([NH:25][N:26]1[CH:30]([CH2:31][CH2:32][CH:33]=[O:34])[C:29](=[O:36])[O:28][CH2:27]1)(=[O:23])=[O:24]

Participants

8

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 16710494Lithium tri-tert-butoxyaluminohydrideHCID 18989348HCID 18989348, compound

Product 1

HCID 18989310HCID 18989310, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1.4 ml (18.2 mmol) of dry dimethylformamide were introduced into 50 ml of methylene chloride and, at 0° C. under an inert gas atmosphere, 2.0 ml (28.2 mmol) of oxalyl chloride in 70 ml of methylene chloride were added dropwise. The mixture was stirred at 0° C. for 30 min and then the solvent was removed under reduced pressure. The remaining white salt (highly hygroscopic) was suspended in 120 ml of THF/acetonitrile (1:1) and cooled to -30° C. To this were added dropwise 5.6 g (16 mmol) of 3-[3-(2-naphthalenesulfonylamino)oxazolidin-5-on-4-yl]propionic acid together with 1.07 ml (16 mmol) of pyridine in 30 ml of THF, and the mixture was then stirred at -20° C. for 20 min. The mixture was subsequently cooled to -75° C., 307 mg of cuprous iodide were added, then a solution of 5.6 g (21.8 mmol) of lithium tri-tert-butoxyaluminum hydride in 20 ml of THF was slowly added dropwise, and the mixture was stirred at this temperature for 1 h. Quenching was then carried out at -75° C. with 30 ml of 2N hydrochloric acid and, after the mixture had warmed to room temperature, the solvent was removed under reduced pressure, the residue was taken up in methylene chloride, the Cu salts were removed by filtration, and the organic phase was washed three times with water, dried over magnesium sulfate and concentrated under reduced pressure. 5.4 g of slightly impure 3-[3-(2-naphthalenesulfonylamino)oxazolidin-5-on-4-yl]propanal were obtained which were rapidly processed further because of the low stability.

Workup

  1. additionwere added dropwise
  2. customthe solvent was removed under reduced pressure
  3. temperaturecooled to -30° C
  4. stirringthe mixture was then stirred at -20° C. for 20 min
  5. temperatureThe mixture was subsequently cooled to -75° C.
  6. stirringthe mixture was stirred at this temperature for 1 h
  7. customQuenching
  8. customwas then carried out at -75° C. with 30 ml of 2N hydrochloric acid
  9. temperatureafter the mixture had warmed to room temperature
  10. customthe solvent was removed under reduced pressure
  11. customthe Cu salts were removed by filtration
  12. washthe organic phase was washed three times with water
  13. dry with materialdried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-89e4a56e8f874160bd29b0088699bfc8
Source dataset
uspto-grants-1996_02
Patent number
US05489583

Reaction notes

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