Pyridine → HCID 66685413, compound

HRID 409645Notes

Reaction equation

HRID 409645 reaction equation
[CH2:1]([O:7][C:8](=O)[CH2:9][NH:10][C:11](=O)[C:12]([O:14][CH3:15])=[O:13])[CH2:2][CH2:3]/[CH:4]=[CH:5]/[CH3:6].N1C=CC=CC=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH3:6][C:5]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[N:10][CH:9]=[C:8]2[O:7][CH2:1][CH2:2][CH2:3][C:4]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86683903HCID 86683903, compound

Product 1

HCID 66685413HCID 66685413, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-Methyl 2-((2-(hex-4-en-1-yloxy)-2-oxoethyl)amino)-2-oxoacetate (0.24 g, 1 eq) and DCM (2.4 mL) were added to a vessel with stirring followed by the addition of pyridine (95 mg, 1.2 eq). Tf2O (0.42 g, 1.5 eq) was then added over 45 min at ambient temperature and the mixture was stirred at ambient temperature for 48 h. The mixture was washed with 20 wt % aqueous NaOAc (2×1.5 mL), 10 wt % aqueous citric acid (3×1.5 mL), and water (1×1.5 mL). The organic layer was then concentrated under reduced pressure to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ ppm 8.10 (s, 1H), 4.15-4.25 (m, 2H), 3.94 (s, 3H), 2.71 (t, J=6.56 Hz, 2H), 2.47 (s, 3H), 2.00-2.18 (m, 2H); 13C NMR (75 MHz, CDCl3) δ ppm 166.71, 153.50, 138.69, 136.72, 135.67, 130.36, 65.93, 52.35, 22.18, 21.49, 14.57; HRMS (M+H) m/z, calcd for C11H14NO3, 208.0974; found 208.0981.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 48 h
  2. washThe mixture was washed with 20 wt % aqueous NaOAc (2×1.5 mL), 10 wt % aqueous citric acid (3×1.5 mL), and water (1×1.5 mL)
  3. concentrationThe organic layer was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-da71c7dc5d0d42a8ab53f899e4ed2b87
Source dataset
uspto-grants-2014_06
Patent number
US08759523B2

Reaction notes

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