Trifluoroacetic acid → HCID 86707293, compound

HRID 576087Notes

Reaction equation

HRID 576087 reaction equation
FC(F)(F)C(O)=O.COC1C=C(OC)C=CC=1C[N:13]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][N:21]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:20]2)(=[O:16])=[O:15].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:38][C:35]1[CH:34]=[CH:33][C:32]([NH:13][S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][N:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:20]3)(=[O:16])=[O:15])=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86707294HCID 86707294, compound

Product 1

HCID 86707293HCID 86707293, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added to a solution of N-(2,4-dimethoxybenzyl)-N-(4-fluorophenyl)-2-phenyl-2,3-dihydro-1H-isoindole-5-sulfonamide obtained (135 mg) in chloroform (4.5 mL) while cooling in ice, 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 ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by NH silica gel column chromatography (chloroform only→chloroform:methanol=19:1). To the resulting crude compound were added ethyl acetate, diethyl ether and hexane, and the mixture was powdered and then collected by filtration to afford the title compound as a light gray powder (74 mg).

Workup

  1. temperaturewhile cooling in ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe resulting residue was purified by NH silica gel column chromatography (chloroform only→chloroform
  8. additionTo the resulting crude compound were added ethyl acetate, diethyl ether and hexane
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-14d55e8b926349339707f0412b3b99d9
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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