Acetic Acid → HCID 12035121, compound

HRID 1767567Notes

Reaction equation

HRID 1767567 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([O:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH:15]=[CH:16][N+:17]([O-:19])=[O:18])[C:7]=2[N:20]=1.C(Cl)(Cl)Cl.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([O:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])[C:7]=2[N:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 69417908HCID 69417908, compound

Product 1

HCID 12035121HCID 12035121, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Under argon and in an anhydrous medium, 340 mg (1.23 mmol) of the compound obtained in Step H are suspended in 7 ml of isopropanol and 21 ml of chloroform in the presence of 810 mg of 230-400 mesh silica; 234 mg (6.18 mmol) of sodium borohydride are added slowly. After 2 hours' stirring at room temperature, acetic acid is added and the reaction mixture is filtered through a glass frit. After removal of the solvents by evaporation, the residue is diluted in dichloromethane and washed with water. The organic phase is then dried over magnesium sulphate, filtered, concentrated and purified by flash chromatography over silica gel (eluant:ethyl acetate/petroleum ether, 6:4) to yield the title compound in the form of a yellow solid.

Workup

  1. filtrationthe reaction mixture is filtered through a glass frit
  2. customAfter removal of the solvents
  3. customby evaporation
  4. additionthe residue is diluted in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic phase is then dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by flash chromatography over silica gel (eluant:ethyl acetate/petroleum ether, 6:4)

Sources & evidence

ORD record
ord-62f9616cbf1449f6ab3c7e87e9a1a124
Source dataset
uspto-grants-2007_06
Patent number
US07235550B2

Reaction notes

Loading…