HCID 10172554, compound → (5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-[4-(fluoromethyl)-1H-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one

HRID 1268985Notes

Reaction equation

HRID 1268985 reaction equation
COCCN[S](F)(F)([F:12])NCCOC.[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][C@H:31]([CH2:33][N:34]3[CH:38]=[C:37]([CH2:39]O)[N:36]=[N:35]3)[O:30][C:29]2=[O:41])[CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1>ClCCl>[F:15][C:16]1[CH:17]=[C:18]([N:28]2[CH2:32][C@H:31]([CH2:33][N:34]3[CH:38]=[C:37]([CH2:39][F:12])[N:36]=[N:35]3)[O:30][C:29]2=[O:41])[CH:19]=[CH:20][C:21]=1[N:22]1[CH:26]=[C:25]([CH3:27])[N:24]=[CH:23]1

Participants

4

Reactant 2

HCID 10172554HCID 10172554, compoundHCID 178496052HCID 178496052, compound

Product 1

HCID 10126360(5R)-3-[3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-[4-(fluoromethyl)-1H-1,2,3-triazol-1-ylmethyl]oxazolidin-2-oneYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bis[(2-methoxyethyl)amino]sulfur trifluoride (150 μl, 0.81 mmol) was added to a solution of (5R)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]-5-[4-(hydroxymethyl)-1H-1,2,3-triazol-1-ylmethyl]-1,3-oxazolidin-2-one (Example 48) (222 mg, 0.60 mmol) in dichloromethane (2 ml) at −78° C. The reaction mixture was allowed to gradually warm to room temperature. After 20 hours, the reaction mixture was heated to 40° C. for 3 hours before cooling to room temperature and quenching with methanol. Chromatography on silica gel with 7.5% methanol in dichloromethane gave 36 mg of product.

Workup

  1. temperaturethe reaction mixture was heated to 40° C. for 3 hours
  2. temperaturebefore cooling to room temperature
  3. customquenching with methanol

Sources & evidence

ORD record
ord-4fec0956ee7a4628bcbd9ff2728bb2cd
Source dataset
uspto-grants-2007_04
Patent number
US07199143B2

Reaction notes

Loading…