2,6-Lutidine → (5R)-3-[4-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-fluorophenyl]-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

HRID 1371832Notes

Reaction equation

HRID 1371832 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]3)[O:11][C:10]2=[O:21])=[CH:5][C:4]=1[F:22])#[CH:2].[N:23]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[N+:24]=[N-:25].N1C(C)=CC=CC=1C>C(#N)C.[Cu](I)I>[CH2:26]([N:23]1[CH:2]=[C:1]([C:3]2[CH:8]=[CH:7][C:6]([N:9]3[CH2:13][C@H:12]([CH2:14][N:15]4[CH:19]=[C:18]([CH3:20])[N:17]=[N:16]4)[O:11][C:10]3=[O:21])=[CH:5][C:4]=2[F:22])[N:25]=[N:24]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 12152Benzyl azideHCID 58626911(5R)-3-(4-Ethynyl-3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one2×

Product 1

HCID 10071508(5R)-3-[4-(1-Benzyl-1H-1,2,3-triazol-4-yl)-3-fluorophenyl]-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-oneYield 26%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

(5R)-3-(4-Ethynyl-3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 9, 40 mg, 0.133 mmol), azidomethyl-benzene(21.2 mg, 0.16 mmol), copper iodide (2.5 mg, 0.013 mmol) and 2,6-lutidine were mixed in dry acetonitrile (2 mL) and stirred at room temperature for over night. The reaction mixture was filtered through a 0.45 μm membrane, the filtrate was concentrated to an oil and purified by reverse phase chromatography with 5%˜95% MeCN in H2O (0.1% TFA). The product was obtained as a colourless solid (15 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a 0.45 μm membrane
  2. concentrationthe filtrate was concentrated to an oil
  3. custompurified by reverse phase chromatography with 5%˜95% MeCN in H2O (0.1% TFA)

Sources & evidence

ORD record
ord-1841c135e4274872a9bb45e39d0715a0
Source dataset
uspto-grants-2007_01
Patent number
US07157482B2

Reaction notes

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