Benzene → HCID 68697266, compound

HRID 1378693Notes

Reaction equation

HRID 1378693 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:13][CH2:14][CH:15]([CH2:17][OH:18])[OH:16].C1C=CC=CC=1.[F:25][C:26]1[CH:27]=[C:28]([N:39]2[CH2:43][C@H:42]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[O:41][C:40]2=[O:49])[CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1>O>[F:25][C:26]1[CH:27]=[C:28]([N:39]2[CH2:43][C@H:42]([CH2:44][NH:45][C:46](=[O:48])[CH3:47])[O:41][C:40]2=[O:49])[CH:29]=[CH:30][C:31]=1[N:32]1[CH2:33][CH2:34][C:35]2([O:16][CH:15]([CH2:17][OH:18])[CH2:14][O:13]2)[CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 753GlycerolHCID 521998p-Toluenesulfonic acid monohydrateHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamide

Product 1

HCID 68697266HCID 68697266, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Para-toluenesulfonic acid monohydrate (299 mg) and glycerol (0.21 ml) were added successively to a benzene suspension (10 ml) of 500 mg of the (S)-N-{3-[3-fluoro-4-(4-oxo-piperidin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (Compound No. 7) which was synthesized in Example 3, and the mixture was heated under reflux for 4 h, with water being removed continuously by means of a water separator. After the reaction mixture was cooled to room temperature, a saturated aqueous sodium hydrogencarbonate solution was added and the mixture was stirred. Thereafter, the solution was extracted with methylene chloride and the organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum and the residue was purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1) to afford the title compound (510 mg) in a yield of 84%.

Workup

  1. custom7) which was synthesized in Example 3
  2. temperaturethe mixture was heated
  3. customremoved continuously by means of a water separator
  4. additiona saturated aqueous sodium hydrogencarbonate solution was added
  5. extractionThereafter, the solution was extracted with methylene chloride
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under vacuum
  9. customthe residue was purified by silica gel column chromatography (solvent: chloroform/methanol=50/1-25/1)

Sources & evidence

ORD record
ord-0f872472955d4b32868ff5f866f97bd2
Source dataset
uspto-grants-1997_09
Patent number
US05668286

Reaction notes

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