3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(azidomethyl)-oxazolidin-2-one → (5S)-5-(Aminomethyl)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one

HRID 1452570Notes

Reaction equation

HRID 1452570 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:14]2[CH2:18][CH:17]([CH2:19][N:20]=[N+]=[N-])[O:16][C:15]2=[O:23])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]1>CO.C(OCC)(=O)C.[Pd]>[NH2:20][CH2:19][C@@H:17]1[O:16][C:15](=[O:23])[N:14]([C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]3)=[C:2]([F:1])[CH:3]=2)[CH2:18]1

Participants

4

Reactant 1

HCID 765562093-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(azidomethyl)-oxazolidin-2-one2×

Product 1

HCID 57526957(5S)-5-(Aminomethyl)-3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-1,3-oxazolidin-2-oneYield 55.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

3-[3-Fluoro-4-(4-methyl-1,2,3-triazol-1-yl)phenyl]-5-(azidomethyl)-oxazolidin-2-one (Intermediate 17) (2.0 g, 6.30 mmol) was dissolved in methanol/ethyl acetate (50 ml, 1:1) and hydrogenated over palladium on carbon (10%, 0.2 g) at room temperature and normal pressure for 4 hours. The resulting mixture was filtered through the celite and concentrated under reduced pressure to give 1.02 g of the title compound as a solid, which was used without further purification in the next step.

Workup

  1. filtrationThe resulting mixture was filtered through the celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9ce7c362ccc4b8e937b0bfca07bf1bd
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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