Nitrogen → Linezolid

HRID 245321

Reaction equation

HRID 245321 reaction equation
[CH2:1]([N:8]([CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1)CC1C=CC=CC=1)[C:2]1C=CC=CC=1.N#N.[H][H].C(OC(=O)C)(=[O:42])C.C(N(CC)CC)C>[Pd].CC(C)=O>[CH3:2][C:1]([NH:8][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[C:25]([F:35])[CH:24]=2)[CH2:18]1)=[O:42]

Participants

8

Reactant 5

HCID 947NitrogenHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11213668(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 441401LinezolidYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

(S)-5-((dibenzylamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one (0.95 g, 2 mmol) and 0.1 g 10 wt % Pd—C were added to 20 mL acetone and the air was replaced with N2. The reaction went on under 5 Mpa hydrogen at room temperature for 5 hours. After filtered, acetic anhydrid (0.24 g, 2.4 mmol) and triethylamine (2.0 g, 20 mmol) were added and reacted for 2 hours at room temperature. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, most part of the solvent was evaporated, frozen crystallized and filtered to provide the crude product. The crude product was recrystallized with ethyl acetate to provide 0.51 g of linezolid in 75% yield.

Workup

  1. filtrationAfter filtered
  2. customreacted for 2 hours at room temperature
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. custommost part of the solvent was evaporated
  7. temperaturefrozen
  8. customcrystallized
  9. filtrationfiltered
  10. customto provide the crude product
  11. customThe crude product was recrystallized with ethyl acetate

Sources & evidence

ORD record
ord-7d088d57876841848e04e42cad2c39d7
Source dataset
uspto-grants-2014_02
Patent number
US08658789B2

Linked notes

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