N-[(5S)-3-(3-Fluoro-4-(4-azidomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide → N-[(5S)-3-(3-Fluoro-4-(4-aminomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

HRID 2299023Notes

Reaction equation

HRID 2299023 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][N:14]=[N+]=[N-])[N:10]=[CH:9]1>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][NH2:14])[N:10]=[CH:9]1

Participants

5

Reactant 1

HCID 57003668N-[(5S)-3-(3-Fluoro-4-(4-azidomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

Product 1

HCID 57285587N-[(5S)-3-(3-Fluoro-4-(4-aminomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

N-[(5S)-3-(3-Fluoro-4-(4-azidomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide (1.38 g, 3.67 mM) was dissolved in ethanol (60 ml), treated with Lindlar catalyst (5% Pd on CaCO3 partially poisoned with lead, 650 mg), and stirred under an atmosphere of hydrogen under balloon pressure for 4 hours. After filtration through celite, solvent was evaporated to give the title product as a gum, pure enough for further work (1.3 g).

Workup

  1. filtrationAfter filtration through celite, solvent
  2. customwas evaporated

Sources & evidence

ORD record
ord-12f6d307cb7a49ccb69b4609d9b61719
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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