Triethylamine → Trifluoro-methanesulfonic acid 1-cyclopropyl-2-oxo-1,2-dihydro-pyridin-4-yl ester

HRID 470523Notes

Reaction equation

HRID 470523 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH:16]1([N:19]2[CH:24]=[CH:23][C:22](O)=[CH:21][C:20]2=[O:26])[CH2:18][CH2:17]1.CCN(CC)CC>ClCCl>[CH:16]1([N:19]2[CH:24]=[CH:23][C:22]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:21][C:20]2=[O:26])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 59635643HCID 59635643, compound

Product 1

HCID 59635747Trifluoro-methanesulfonic acid 1-cyclopropyl-2-oxo-1,2-dihydro-pyridin-4-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic anhydride (0.12 mL) was added to a flask charged with a stir bar, 1-cyclopropyl-4-hydroxy-1H-pyridin-2-one (0.10 g), NEt3 (0.24 mL), and dichloromethane (8 mL) and chilled in an ice/EtOH bath. The resulting mixture was stirred with cooling for 2 h and at ambient temperature for another 2 h. Then, the solution was diluted with dichloromethane and washed in succession with water, aqueous NaHCO3 solution, and water. The organic solution was dried (MgSO4), the solvent was removed, and the residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->90:10) to afford the title compound as a resin-like solid. Yield: 0.07 g (36% of theory). Mass spectrum (ESI+): m/z=284 [M+H]+.

Workup

  1. additioncharged with a stir bar
  2. washwashed in succession with water, aqueous NaHCO3 solution, and water
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customthe solvent was removed
  5. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->90:10)

Sources & evidence

ORD record
ord-7c77edf1275149c2a3f526f4602bde92
Source dataset
uspto-grants-2014_01
Patent number
US08629138B2

Reaction notes

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