Trifluoroacetic acid → HCID 86707291, compound

HRID 576086Notes

Reaction equation

HRID 576086 reaction equation
C1(OC)C=CC=CC=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:53])[CH2:20][N:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([S:31]([N:34](CC4C=CC(OC)=CC=4OC)[C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=4)(=[O:33])=[O:32])[CH:27]=3)[CH2:22]2)=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:9]([C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:53])[CH2:20][N:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([S:31]([NH:34][C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=4)(=[O:32])=[O:33])[CH:27]=3)[CH2:22]2)=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 86707292HCID 86707292, compound

Product 1

HCID 86707291HCID 86707291, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Anisole (3 mL) was added to a solution of 2-[2-(4-tert-butylphenyl)-2-oxoethyl]-N-(2,4-dimethoxybenzyl)-N-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline-6-sulfonamide obtained (258 mg) in chloroform (5 mL), and the mixture was cooled in ice. Trifluoroacetic acid (1 mL) was added thereto and the mixture was stirred at the same temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→3:2) to afford the title compound as a pale yellow amorphous substance (153 mg).

Workup

  1. temperaturethe mixture was cooled in ice
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered off
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→3:2)

Sources & evidence

ORD record
ord-f024753887444894bb6c2bdca804cf92
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

Loading…