Sodium Bicarbonate → HCID 86698561, compound

HRID 1846154Notes

Reaction equation

HRID 1846154 reaction equation
[F:1][C:2]([F:21])([F:20])[S:3]([O:6][C:7]1[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[N:10]=[C:9]2[N:16]([CH3:19])[CH2:17][CH2:18][C:8]=12)(=[O:5])=[O:4].C([O-])(O)=O.[Na+]>CS(C)=O.CC(C)=O>[F:21][C:2]([F:1])([F:20])[S:3]([O:6][C:7]1[C:12]([CH:13]=[O:14])=[C:11]([CH3:15])[N:10]=[C:9]2[N:16]([CH3:19])[CH2:17][CH2:18][C:8]=12)(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86698559HCID 86698559, compound

Product 1

HCID 86698561HCID 86698561, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 134 mg of alcohol 30 in 2 mL of DMSO and 2 mL of acetone was added 116 mg of IBX. The reaction mixture was stirred at room temperature for 16 h then cooled to 0° C., 5 mL of a mixture of 5% NaHCO3 and 5% of NaS2O3 was added by syringe slowly. After stirred for additional 20 min the mixture was extracted with three portions of 5 mL of ethyl acetate. The combined organic layer was washed with brine and dried over MgSO4. After the solvent was removed under diminished pressure, the residue was purified by flash chromatography on a silica gel column (15×2 cm). Elution with 1:10 EtOAc-hexanes gave product 31 as white crystal: yield 121 mg, (91%). Silica gel TLC Rf 0.20 (1:4 EtOAc-hexanes); 1H NMR (CDCl3, ppm): δ 2.70 (s, 3H), 3.09 (s, 3H), 3.18 (t, J=8.5 Hz, 2H), 3.72 (t, J=8.5 Hz, 2H), 10.09 (s, 1H). 13C NMR (CDCl3, ppm): 623.21, 24.06, 31.48, 51.19, 112.28, 112.40, 120.01, 151.18, 165.51, 166.54, 185.22; 19F NMR (CDCl3, ppm): δ−73.54 (s, 3F); HRMS (APCI+) calculated for C11H12N2O4SF3 (M+H+) 325.0470. found 325.0465.

Workup

  1. temperaturethen cooled to 0° C.
  2. stirringAfter stirred for additional 20 min the mixture
  3. extractionwas extracted with three portions of 5 mL of ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter the solvent was removed under diminished pressure
  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-55a5359490954d5eac17ab4700f88ade
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

Loading…