Tetrahydrofuran → HCID 68445452, compound

HRID 1838401Notes

Reaction equation

HRID 1838401 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[C:8]2=[N:9][CH:10]=[C:11](SC)[N:12]=[C:7]2[CH:6]=1)=[O:4].O[O:25][S:26]([O-:28])=O.[K+].O1CCC[CH2:31]1>CO.O>[CH3:1][O:2][C:3]([C:5]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)[C:8]2=[N:9][CH:10]=[C:11]([S:26]([CH3:31])(=[O:28])=[O:25])[N:12]=[C:7]2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfite2×HCID 68443794HCID 68443794, compound

Product 1

HCID 68445452HCID 68445452, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

To a suspension of the compound obtained in Example 34 (7) (1.06 g) in tetrahydrofuran (40 ml), methanol (40 ml) and water (20 ml), OXONE (2.16 g) was added at 0° C. and the mixture was stirred at 15 to 30° C. for 4 hours. Further, OXONE (1.08 g) was added thereto and the mixture was stirred at 15 to 30° C. for 1 hour. After completion of the reaction, the reaction solution was concentrated and poured into a saturated aqueous sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate, washed with a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting residue was then separated using silica gel column chromatography (ethyl acetate:hexane=1:2 and 2:1) to obtain 852 mg (73%) of the desired product as a pale yellow crystal.

Workup

  1. additionwas added at 0° C.
  2. stirringthe mixture was stirred at 15 to 30° C. for 1 hour
  3. customAfter completion of the reaction
  4. concentrationthe reaction solution was concentrated
  5. additionpoured into a saturated aqueous sodium hydrogencarbonate solution
  6. extractionThe mixture was extracted with ethyl acetate
  7. washwashed with a saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting residue was then separated

Sources & evidence

ORD record
ord-f1b978bf1eea4c98ae854dd12bc76524
Source dataset
uspto-grants-2004_01
Patent number
US06673797B1

Reaction notes

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