Pyridine → HCID 53806064, compound

HRID 617753Notes

Reaction equation

HRID 617753 reaction equation
[C@H:1]12[CH2:24][C@H:4]([N:5]([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][N:19]=[N+]=[N-])[O:15][C:14]4=[O:22])=[CH:9][C:8]=3[F:23])[CH2:6]1)[CH2:3][O:2]2.N1C=CC=CC=1.[C:31](OC(=O)C)(=[O:33])[CH3:32].O1CCNC1=O>CO.C(Cl)Cl.[Pd].CO.C(Cl)(Cl)Cl>[C@H:1]12[CH2:24][C@H:4]([N:5]([C:7]3[CH:12]=[CH:11][C:10]([N:13]4[CH2:17][C@H:16]([CH2:18][NH:19][C:31](=[O:33])[CH3:32])[O:15][C:14]4=[O:22])=[CH:9][C:8]=3[F:23])[CH2:6]1)[CH2:3][O:2]2

Participants

9

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 739492-OxazolidinoneHCID 53868579HCID 53868579, compound

Product 1

HCID 53806064HCID 53806064, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent2×

Procedure

A solution of (R)-[[3-[4-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]azide (0.652 g, 1.96 mmol) in MeOH (20 mL) and CH2Cl2 (10 mL) was treated with 10% palladium/carbon (0.095 g) under a N2 stream. The atmosphere was then replaced with H2 (balloon) by repeated evacuation and filling and the mixture stirred at ambient temperature under H2. After 3 h, TLC analysis (5% MeOH/CHCl3) revealed the reduction to be complete. The reaction mixture was filtered through Celite® and the filtrate concentrated under reduced pressure. The crude 5-(aminomethyl)oxazolidinone was dissolved in CH2C2 (20 mL) and treated with pyridine (0.190 mL, 2.35 mmol) and then acetic anhydride (0.222 mL, 2.35 mmol). After 0.5 h, TLC analysis (5% MeOH/CHCl3) indicated the acetylation to be complete. The reaction mixture was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo to give an off-white solid. Chromatography over silica gel (70 g), eluting with a gradient of 1-3% MeOH/CHCl3, afforded, after concentration of appropriate fractions, 0.517 g (76%) of the title oxazolidinone antibacterial agent as a white solid with mp 60-65° C. and MS(EI) 349 (M+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutionThe crude 5-(aminomethyl)oxazolidinone was dissolved in CH2C2 (20 mL)
  4. waitAfter 0.5 h
  5. washThe reaction mixture was washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give an off-white solid
  10. washChromatography over silica gel (70 g), eluting with a gradient of 1-3% MeOH/CHCl3
  11. customafforded

Sources & evidence

ORD record
ord-dccf9c036b1f40df9b11faea31585942
Source dataset
uspto-grants-1999_09
Patent number
US05952324

Reaction notes

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