Dimethyl Sulfoxide → HCID 25230267, compound

HRID 2274334Notes

Reaction equation

HRID 2274334 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:25])[CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8](=[O:25])[CH2:9][O:10][C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)HCID 46911039HCID 46911039, compound

Product 1

HCID 25230267HCID 25230267, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 5-{4-[2-(3-fluorophenyl)-2-hydroxyethoxy]benzyl}-1,3-thiazolidine-2,4-dione (0.62 g, 1.70 mmol) in DCM (15 mL) was added DMSO (0.5 mL) and the solution was cooled to 0° C. Added phosphorus pentoxide (0.49 g, 1.72 mmol) followed by triethylamine (1.1 mL, 7.72 mmol). The reaction mixture was allowed to slowly warm to RT. After 2 hours, HPLC shows that the reaction was complete. Added water and separated phases. The pH of the aqueous phase was adjusted to ca. 7 with 2M NaOH and the aqueous phase was then extracted with EtOAc. The combined extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting white solid was chromatographed on a small silica gel column eluting with 10% EtOAc/DCM. Fractions containing product were combined and evaporated in vacuo to give 0.25 g (40%) of the title compound as a white solid. MS (ESI−) for C18H14FNO4S m/z 358.0 (M−H)−.

Workup

  1. temperatureto slowly warm to RT
  2. customAdded water and separated phases
  3. extractionthe aqueous phase was then extracted with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting white solid was chromatographed on a small silica gel column
  9. washeluting with 10% EtOAc/DCM
  10. additionFractions containing product
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-21590d97f2404fa4874e551bc9ddf6ed
Source dataset
uspto-grants-2015_09
Patent number
US09126959B2

Reaction notes

Loading…