Pyridine → HCID 15381194, compound

HRID 1418647Notes

Reaction equation

HRID 1418647 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][N:20]=[N+]=[N-])[O:16][C:15]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:11][CH:10]([O:12][CH3:13])[CH2:9]1.[H][H].N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>[Pd].C(OCC)(=O)C.CCCCCC.CO.C(Cl)(Cl)Cl.CO.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][C@H:17]([CH2:19][NH:20][C:32](=[O:34])[CH3:33])[O:16][C:15]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:11][CH:10]([O:12][CH3:13])[CH2:9]1

Participants

9

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 15381193HCID 15381193, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15381194HCID 15381194, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolventHCID 21226206Ethyl acetate hexaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A solution of (R)-[[3-[3-fluoro-4-(3-methoxy-1-azetidinyl)phenyl]-2oxo-5-oxazolidinyl]methyl]azide (0.393 g, 1.22 mmol) in 5:1 methanol/dichloromethane (20 mL) was treated with 10% palladium on carbon (0.030 g) under a nitrogen stream. The atmosphere was then replaced with hydrogen (balloon). After stirring 3 hours under hydrogen, the reduction was judged to be complete by TLC analysis (5% methanol/chloroform). The reaction mixture was filtered through Celite® and concentrated under reduced pressure. The crude 5-(aminomethyl)oxazolidinone was dissolved in dichloromethane (15 mL) and treated with pyridine (0.118 mL, 1.46 mmol) and acetic anhydride (0.138 mL, 1.46 mmol) under a nitrogen atmosphere at ambient temperature. After 2 h, the reaction was judged to be complete by TLC. The reaction mixture was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. Chromatography over silica gel (50 g), eluting with a gradient of 1-3% methanol/chloroform, afforded, after concentration of appropriate fractions, 0.281 g (68%) of the title antibacterial agent as a white solid. An analytical sample, prepared by recrystallization from 2:1 ethyl acetate/hexane, was a white solid with mp 160°-161.5° C. and MS(EI) 337 (M+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude 5-(aminomethyl)oxazolidinone was dissolved in dichloromethane (15 mL)
  4. waitAfter 2 h
  5. washThe reaction mixture was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. washChromatography over silica gel (50 g), eluting with a gradient of 1-3% methanol/chloroform
  10. customafforded

Sources & evidence

ORD record
ord-78a88b75c5c54dec8d962e7fe4247dd1
Source dataset
uspto-grants-1999_03
Patent number
US05883093

Reaction notes

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