Chloroform → HCID 21922548, compound

HRID 1244792Notes

Reaction equation

HRID 1244792 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5](/[CH:6]=[CH:7]/[S:8]([N:11]([CH2:18][CH:19](OCC)[O:20]CC)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[S:8]([N:11]([CH2:18][CH:19]=[O:20])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:9])=[O:10])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22565205HCID 22565205, compound

Product 1

HCID 21922548HCID 21922548, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed solution of the compound obtained in Step 1 (2.00 g), chloroform (9.5 ml) and water (9.5 ml) was added trifluoroacetic acid (13.5 ml) under cooling with ice water. The reaction mixture was stirred at room temperature for 4 hours, adjusted to pH 8 with saturated aqueous solution of sodium hydrogencarbonate and extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and thereafter the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=2:1) to obtain the title compound (1.27 g).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-8c4ebdefedbc4d9c8e083cbba4db2424
Source dataset
uspto-grants-2006_10
Patent number
US07122662B2

Reaction notes

Loading…