Trifluoroacetic acid → HCID 66941806, compound

HRID 1360812Notes

Reaction equation

HRID 1360812 reaction equation
FC(F)(F)C(O)=O.CC([NH:16][S:17]([C:20]1[CH:21]=[N:22][C:23]([C:26]2[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=2[O:34][CH3:35])=[CH:24][CH:25]=1)(=[O:19])=[O:18])(C)CC(C)(C)C>ClCCl>[CH3:33][O:32][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([O:34][CH3:35])[C:26]=1[C:23]1[N:22]=[CH:21][C:20]([S:17]([NH2:16])(=[O:19])=[O:18])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66942232HCID 66942232, compound

Product 1

HCID 66941806HCID 66941806, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.6 ml, 47 mmol) was added to a solution of 6-(2,6-Dimethoxy-phenyl)-pyridine-3-sulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (1.90 g, 4.7 mmol) in 40 ml dichloromethane and stirred at room temperature (monitored by TLC). The mixture was evaporated to dryness, taken up in 10 ml ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was evaporated to dryness and the residue was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient) to return 1.28 g of the title compound as an off-white solid, m/z=295 (ES+), 293 (ES−).

Workup

  1. customThe mixture was evaporated to dryness
  2. washwashed with aqueous sodium bicarbonate
  3. customThe organic layer was evaporated to dryness
  4. customthe residue was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-9e1fd0d022de442a83b444927bc64626
Source dataset
uspto-grants-2011_02
Patent number
US07879884B2

Reaction notes

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