Trifluoromethanesulfonic anhydride → Trifluoromethanesulfonate

HRID 1376857Notes

Reaction equation

HRID 1376857 reaction equation
S1C=CC=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1.[O:12]([S:20]([C:23](F)(F)F)(=O)=O)[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14]>C(Cl)Cl>[F:17][C:16]([F:19])([F:18])[S:13]([O-:15])(=[O:14])=[O:12].[S:20]1[C:23]2=[NH+:7][CH:8]=[CH:9][CH:10]=[C:11]2[CH:6]=[CH:2]1

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 768322-(2'-Thienyl)pyridine

Product 2

HCID 2758875TrifluoromethanesulfonateHCID 18359070Thieno [2,3-b]pyridinium

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an inert atmosphere, 190 mg of the product of Step B, 5 ml of methylene chloride, and 0.126 g of thienyl pyridine were mixed together and stirred for 5 minutes. Then at -70° C., 0.140 ml of a solution of (CF3SO2)2O in methylene chloride was added dropwise followed by stirring for 50 minutes while allowing the temperature to rise to -50° C. After concentrating to dryness under a good vacuum, methylene chloride was added with stirring followed by washing with an N aqueous solution of hydrochloric acid, and again concentrating to dryness by distilling under reduced pressure. The residue was chromatographed over silica and eluted with a mixture of methylene chloride and methanol (9/1) to obtain 136 mg of syn isomer of trifluoromethane sulfonate of 1,1-dimethyl ethyl]-methyl]-thieno [2,3-b]pyridinium (6S, 7S ΔZ)l-[[7-((2-triphenylmethylamino)-4-thiazolyl [[2-bromo-2-propenyloxy)-imino]-acetamido]-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-3-yl]-2-carboxylate

Workup

  1. stirringby stirring for 50 minutes
  2. customto rise to -50° C
  3. concentrationAfter concentrating to dryness under a good vacuum, methylene chloride
  4. additionwas added
  5. stirringwith stirring
  6. washby washing with an N aqueous solution of hydrochloric acid
  7. concentrationagain concentrating to dryness
  8. distillationby distilling under reduced pressure
  9. customThe residue was chromatographed over silica
  10. washeluted with a mixture of methylene chloride and methanol (9/1)

Sources & evidence

ORD record
ord-4436de340caa44ea8612d76335822d45
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

Loading…