TfOH-TFA → 5-Chloro-pyridine-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amide

HRID 1783417Notes

Reaction equation

HRID 1783417 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]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][N:35]=2)(=[O:33])=[O:32])[C:22]1=[O:41]>ClCCl>[F:29][C:25]1([F:28])[CH2:26][CH2:27][NH:21][C:22](=[O:41])[C@H:23]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][N:35]=2)(=[O:32])=[O:33])[CH2:24]1

Participants

4

Reactant 2

HCID 18539426TfOH-TFAHCID 866107455-Chloro-pyridine-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide

Product 1

HCID 866107465-Chloro-pyridine-2-sulfonic acid ((R)-5,5-difluoro-2-oxo-azepan-3-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture containing trifluoroacetic acid/trifluoromethanesulfonic acid (5:2 v/v, 2.44 ml) was added to 5-chloro-pyridine-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide (0.37 g, 0.76 mmol) in dichloromethane (20 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-ethylacetate, 1:1-0:1); white solid 0.22 g (84%); MS: m/e=340.0 (MH+).

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-ethylacetate, 1:1-0:1)

Sources & evidence

ORD record
ord-a767e2cc465548bba826aba987932013
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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