Trifluoroacetic acid → 4-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 1783394Notes

Reaction equation

HRID 1783394 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][C@@H:27]2[CH2:33][C:32]([F:35])([F:34])[CH2:31][CH2:30][N:29](CC3C=CC(OC)=CC=3OC)[C:28]2=[O:47])(=[O:25])=[O:24])=[CH:19][CH:18]=1>C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:26][C@@H:27]2[CH2:33][C:32]([F:34])([F:35])[CH2:31][CH2:30][NH:29][C:28]2=[O:47])(=[O:24])=[O:25])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 575899044-Chloro-N-[(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-benzenesulfonamide

Product 1

HCID 575899014-Chloro-N-((R)-5,5-difluoro-2-oxo-azepan-3-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cocktail containing 40% trifluoroacetic acid, 1% trifluoromethanesulfonic acid in CH2Cl2 (20 ml) was added to 4-chloro-N-[(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-benzenesulfonamide (0.5 g, 1.0 mmol). After 30 min the reaction mixture was concentrated and the residue was dissolved in ethyl acetate and washed with water, NaHCO3 solution, 1 M KHSO4 solution, brine, dried (MgSO4.2H2O), filtered, concentrated under reduce pressure and purified over silica gel (CH2Cl2/MeOH 95:5 v/v): white solid 0.74 g (78%);

Workup

  1. concentrationAfter 30 min the reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, NaHCO3 solution, 1 M KHSO4 solution, brine
  4. dry with materialdried (MgSO4.2H2O)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified over silica gel (CH2Cl2/MeOH 95:5 v/v)

Sources & evidence

ORD record
ord-f3bb5e9cfc8546aeb6a1f6aa91b6e90b
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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