Hydrogen Peroxide → HCID 86698562, compound

HRID 1846155Notes

Reaction equation

HRID 1846155 reaction equation
[F:1][C:2]([F:21])([F:20])[S:3]([O:6][C:7]1[C:12](C=O)=[C:11]([CH3:15])[N:10]=[C:9]2[N:16]([CH3:19])[CH2:17][CH2:18][C:8]=12)(=[O:5])=[O:4].OO.[C:24]([O-])([OH:26])=[O:25].[Na+]>ClCCl>[CH:24]([O:26][C:12]1[C:7]([O:6][S:3]([C:2]([F:21])([F:1])[F:20])(=[O:5])=[O:4])=[C:8]2[CH2:18][CH2:17][N:16]([CH3:19])[C:9]2=[N:10][C:11]=1[CH3:15])=[O:25]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 86698561HCID 86698561, compound

Product 1

HCID 86698562HCID 86698562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 80 mg (0.24 mmol) of aldehyde 31 in 3 mL of dichloromethane was added 1 mg (0.09 mmol) of SeO2 and 1.5 mL of H2O2 (30% in H2O). The reaction mixture was stirred at room temperature for 16 h then cooled to 0° C., 12 mL of 5% of NaHCO3 was added slowly. The mixture was stirred for additional 20 min then extracted with three portions of 15 mL of ethyl acetate. The combined organic layer was washed with brine and dried over Na2SO4. After solvent was removed, the residue was purified by flash chromatography on a silica gel column (15×2 cm). Elution with 1:10 EtOAc-hexanes gave product 32 as light yellow solid: yield 47.6 mg (57%). Silica gel TLC Rf 0.28 (4:1 EtOAc-hexanes); 1H NMR (CDCl3, ppm): δ 2.25 (s, 3H), 2.94 (s, 3H), 3.08 (t, J=8.4 Hz, 2H), 3.57 (t, J=8.4 Hz, 2H), 8.23 (s, 1H). 13C NMR (CDCl3, ppm): δ 19.21, 23.69, 32.36, 52.10, 113.38, 116.76, 119.95, 126.71, 150.24, 158.20, 162.82; 19F NMR (CDCl3, ppm): δ−73.77 (s, 3F); HRMS (ESI+) calculated for C11H11N2O5SF3 (M+H+) 340.0414. found 340.0413.

Workup

  1. temperaturethen cooled to 0° C.
  2. stirringThe mixture was stirred for additional 20 min
  3. extractionthen extracted with three portions of 15 mL of ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter solvent was removed
  7. customthe residue was purified by flash chromatography on a silica gel column (15×2 cm)
  8. washElution with 1:10 EtOAc-hexanes

Sources & evidence

ORD record
ord-597215b2894c452592c808e66b868da4
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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