Dimethyl Disulfide → HCID 15453966, compound

HRID 1870285Notes

Reaction equation

HRID 1870285 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH3:30][S:31]SC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]2[C:17]([S:31][CH3:30])=[C:18]([F:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 2724682Lithium diisopropylamideHCID 15453940HCID 15453940, compound

Product 1

HCID 15453966HCID 15453966, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethoxy)-5-fluoro-1,2-benzisoxazole (0.30 g) in tetrahydrofuran (20 ml) was added lithium diisopropylamide (1.50 ml, 1.5 M hexane solution) dropwise with stirring at -70° C. under nitrogen atmosphere, then after being stirred at the same temperature for 15 minutes dimethyldisulphide (0.21 g) was added. The reaction mixture was stirred for 15 minutes at -70° C. and then the temperature was raised to 0° C. The reaction mixture was poured into ice water (40 ml), extracted with ethyl acetate (twice each with 40 ml) and the combined extracts were dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent, to give the title compound (0.32 g, 94% yield) as a colorless powder.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 15 minutes at -70° C.
  3. temperaturethe temperature was raised to 0° C
  4. extractionextracted with ethyl acetate (twice each with 40 ml) and the combined extracts
  5. dry with materialwere dried over anhydrous magnesium sulphate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography with cyclohexane/ethyl acetate (9/1) as an eluent

Sources & evidence

ORD record
ord-05335177bcb84bafa07e1f1c7b6a741e
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

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