Ethyl 2-oxocyclopentanecarboxylate → HCID 178517728, compound

HRID 2374736Notes

Reaction equation

HRID 2374736 reaction equation
Cl.[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]([NH2:14])=[NH:13].[O-]CC.[Na+].C([O:21][C:22]([CH:24]1[CH2:28][CH2:27][CH2:26][C:25]1=O)=O)C>C(O)C>[F:2][C:3]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:10][CH2:11][C:12]1[NH:14][C:25]2[CH2:26][CH2:27][CH2:28][C:24]=2[C:22](=[O:21])[N:13]=1

Participants

5

Reactant 3

HCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 2723922Sodium ethoxideHCID 69003078HCID 69003078, compound

Product 1

HCID 178517728HCID 178517728, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(2,3-difluorophenyl)-propionamidine hydrochloride (Int. A3) (3.90 g, 17.7 mmol) in ethanol (80 ml) was added sodium ethoxide (1.44 g, 21.2 mmol) in portions and resulting slurry stirred at ambient temperature for 1 h. 2-Oxo-cyclopentanecarboxylic acid ethyl ester (3.09 ml, 21.2 mmol) was then added and the mixture refluxed for 2 days. Evaporation of the reaction mixture followed by chromatography (silica, dichloromethane-acetone) gave the title compound (2.76 g, 56%) as a cream solid. 1H-NMR (DMSO) δ 1.94 (2H, m), 2.59 (2H, t), 2.72 (2H, t), 2.82 (2H, t), 3.05 (2H, t), 7.07-7.29 (3H, m), 12.20 (1H, s); MS (APCI+) found (M+1)=277; C15H14F2N2O requires 276.

Workup

  1. customresulting slurry
  2. temperaturethe mixture refluxed for 2 days
  3. customEvaporation of the reaction mixture

Sources & evidence

ORD record
ord-d9eee1e7eb2e4de6bc5aa12923a0eeb7
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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