Imidazole → HCID 57205963, compound

HRID 429880Notes

Reaction equation

HRID 429880 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:13]([CH2:14]OS(C(F)(F)F)(=O)=O)[O:12][C:11](=[O:23])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@@H:13]([CH2:14][N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)[O:12][C:11](=[O:23])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 57206126HCID 57206126, compound

Product 1

HCID 57205963HCID 57205963, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4S, 5R) 4-(3,4-difluorophenyl)-5-(trifluoromethanesulfonyloxymethyl)-oxazolidin-2-one (approximately 1.7 g, 4.6 mmol maximum) in tetrahydrofuran (40 mL) was added imidazole (1.6 g, 23 mmol) and the mixture stirred at ambient temperature 45 min. The volatiles were removed and the residue taken up in ethyl acetate (100 mL), washed with water (2×50 mL), brine (1×50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to provide an oil. The oil was purified by pressurized silica gel chromatography (5-7% methanol in dichloromethane containing 0.5% NH4OH) to provide (4S, 5R) 4-(3,4-difluorophenyl)-5-(imidazol-1-ylmethyl)-oxazolidin-2-one as a white solid.

Workup

  1. customThe volatiles were removed
  2. washwashed with water (2×50 mL), brine (1×50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide an oil
  7. customThe oil was purified by pressurized silica gel chromatography (5-7% methanol in dichloromethane containing 0.5% NH4OH)

Sources & evidence

ORD record
ord-4dbe6215fae343d699748397ba9c9af3
Source dataset
uspto-grants-2001_11
Patent number
US06319932B1

Reaction notes

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