Ethyl Acetate → HCID 178471099, compound

HRID 709837Notes

Reaction equation

HRID 709837 reaction equation
[CH:1]1([CH:4]([C:11]2[C:16]([F:17])=[CH:15][N:14]=[C:13]([O:18]C)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.[Cl-].[NH+]1C=CC=CC=1.C(OCC)(=O)C>CN(C=O)C>[CH:1]1([CH:4]([C:11]2[C:16]([F:17])=[CH:15][N:14]=[C:13]([OH:18])[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 69401Einecs 211-027-4HCID 117760250HCID 117760250, compound

Product 1

HCID 178471099HCID 178471099, compoundYield 126.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Under a nitrogen atmosphere, to a solution of ethyl 3-cyclopropyl-3-(5-fluoro-2-methoxypyridin-4-yl)propanoate (1.38 g) obtained in step A in DMF (2.5 mL) was added pyridinium chloride (5.97 g), and the mixture was stirred at 130° C. for 2 hr. To the reaction mixture was added ethyl acetate at 0° C., and the resulting precipitate was removed by filtration. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (1.65 g) as a pale-yellow oil.

Workup

  1. customthe resulting precipitate was removed by filtration
  2. customThe solvent in the filtrate was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-22cea96455e84184a5ce87b6b748a3a5
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…