Trifluoroacetic acid → HCID 56924473, compound

HRID 1713135Notes

Reaction equation

HRID 1713135 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[NH:9][C:10](=O)OC(C)(C)C)=O.C(OC=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])C.C(O)(C(F)(F)F)=O>C(Cl)(Cl)Cl>[N:9]1[C:4]2[C:3](=[CH:8][CH:7]=[N:6][CH:5]=2)[CH:1]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 221780Ethyl 3-ethoxy-2-propenoateHCID 14177126Tert-butyl 4-formylpyridin-3-ylcarbamate

Product 1

HCID 56924473HCID 56924473, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of tert-butyl 4-formylpyridin-3-ylcarbamate (1.7 g, 7.65 mmol), ethyl 3-ethoxyacrylate (1.27 g, 8.8 mmol) and TFA (5.9 mL, 76.5 mmol) in CHCl3 (30 mL) is heated at reflux for 4 hr. The mixture is cooled and the solvent is removed in vacuo. The residue is dissolved in EtOAc (30 mL) and washed with saturated NaHCO3 solution (20 mL). The organic layer is dried and evaporated. Purification of the residue with flash column with hexane/EtOAc (2:1) gives the title compound as a white solid. MS (M+1): 203.1.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hr
  3. temperatureThe mixture is cooled
  4. customthe solvent is removed in vacuo
  5. dissolutionThe residue is dissolved in EtOAc (30 mL)
  6. washwashed with saturated NaHCO3 solution (20 mL)
  7. customThe organic layer is dried
  8. customevaporated
  9. customPurification of the residue with flash column with hexane/EtOAc (2:1)

Sources & evidence

ORD record
ord-76b77044f1224024995bbddc5f93ef66
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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