TfOH-TFA → N-[(3R)-5,5-difluoro-2-oxoazepan-3-yl]-3,3,3-trifluoro-N-[(6-methoxy-3-pyridinyl)methyl]propane-1-sulfonamide

HRID 1783412Notes

Reaction equation

HRID 1783412 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O.COC1C=C(OC)C=CC=1C[N:21]1[CH2:27][CH2:26][C:25]([F:29])([F:28])[CH2:24][C@@H:23]([N:30]([CH2:40][C:41]2[CH:42]=[N:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[S:31]([CH2:34][CH2:35][C:36]([F:39])([F:38])[F:37])(=[O:33])=[O:32])[C:22]1=[O:49]>ClCCl>[F:29][C:25]1([F:28])[CH2:26][CH2:27][NH:21][C:22](=[O:49])[C@H:23]([N:30]([CH2:40][C:41]2[CH:42]=[N:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)[S:31]([CH2:34][CH2:35][C:36]([F:38])([F:39])[F:37])(=[O:33])=[O:32])[CH2:24]1

Participants

4

Reactant 2

HCID 18539426TfOH-TFAHCID 866107423,3,3-Trifluoro-propane-1-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide

Product 1

HCID 44455643N-[(3R)-5,5-difluoro-2-oxoazepan-3-yl]-3,3,3-trifluoro-N-[(6-methoxy-3-pyridinyl)methyl]propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing trifluoroacetic acid/trifluoromethanesulfonic acid (5:2 v/v, 0.76 ml) was added to 3,3,3-trifluoro-propane-1-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide (0.2 g, 0.24 mmol) in dichloromethane (10 ml). After 2 h the reaction mixture was concentrated under reduced pressure and the residue taken up in ethyl acetate and washed with water, saturated aqueous sodium bicarbonate and brine, dried (Na2SO4), filtered, concentrated under reduced pressure and purified over silica gel (heptane-ethyl acetate, 9:1-0:1): white solid 72 mg (69%);

Workup

  1. concentrationAfter 2 h the reaction mixture was concentrated under reduced pressure
  2. washwashed with water, saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified over silica gel (heptane-ethyl acetate, 9:1-0:1)

Sources & evidence

ORD record
ord-82a6a5a1bb6445d28ca1c7d6942feb56
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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