Dimethylformamide → 5-{4-[2-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)-propoxy]benzyl}thiazolidine-2,4-dione

HRID 2294279Notes

Reaction equation

HRID 2294279 reaction equation
[O:1]([CH2:8][CH:9]([OH:30])[CH2:10][NH:11][CH:12]([CH3:29])[CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][CH:20]2[S:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)[CH:33]=[O:34]>>[O:1]([CH2:8][CH:9]1[O:30][C:33](=[O:34])[N:11]([CH:12]([CH3:29])[CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 15383952HCID 15383952, compound

Product 1

HCID 153839325-{4-[2-(5-Phenoxymethyl-2-oxooxazolidin-3-yl)-propoxy]benzyl}thiazolidine-2,4-dione

Procedure

211 mg of N,N'-carbonyldiimidazole were added to a solution of 500 mg of 5-{4-[2-(3-phenoxy-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Example 3) in 5 ml of anhydrous dimethylformamide, whilst ice-cooling, and the mixture was then stirred at room temperature for 5 hours. At the end of this time, the dimethylformamide was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the resulting residue, which was then extracted with ethyl acetate. The extract was further washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extract by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of ethyl acetate and hexane ranging from 1:1 to 2:1 by volume as the eluent, to give 410 mg of the title compound, melting at 54° C. to 56° C.

Workup

  1. temperaturecooling
  2. customAt the end of this time, the dimethylformamide was removed from the reaction mixture by evaporation under reduced pressure, and water
  3. additionwas added to the resulting residue, which
  4. extractionwas then extracted with ethyl acetate
  5. washThe extract was further washed with an aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ethyl acetate was removed from the
  8. extractionextract by evaporation under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography
  10. washa gradient elution method

Sources & evidence

ORD record
ord-58f66c80b9e545aea8b6306bad3f299f
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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