Sodium Bicarbonate → ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetate

HRID 477831

Reaction equation

HRID 477831 reaction equation
[F:1][C:2]1[C:20]([F:21])=[C:19](F)[C:18]([F:23])=[CH:17][C:3]=1[C:4]([CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])C(OCC)=O)=[O:5].[CH2:24]([O:26][C:27]([N:29]([CH2:31][CH:32]1[O:37][CH2:36][CH2:35][NH:34][CH2:33]1)[CH3:30])=[O:28])[CH3:25].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:24]([O:26][C:27]([N:29]([CH2:31][CH:32]1[CH2:33][N:34]([C:19]2[C:18]([F:23])=[CH:17][C:3]([C:4]([CH2:6][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])=[C:2]([F:1])[C:20]=2[F:21])[CH2:35][CH2:36][O:37]1)[CH3:30])=[O:28])[CH3:25]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 135649731,3-Diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioateHCID 146525772-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine

Product 1

HCID 14652581ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3.36 g of diethyl 2,3,4,5-tetrafluorobenzoylmalonate, 2.22 g of 2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine and 0.84 g of sodium hydrogen carbonate in 13 ml of acetonitrile is refluxed for 5 hours., The reaction mixture is concentrated under reduced pressure, to the obtained residue is added 20 ml of chloroform and it is washed with water. After drying over anhydrous magnesium sulfate, the chloroform is distilled off under reduced pressure and to the residue are added 20 mg of p-toluenesulfonic acid and 20 ml of water. After refluxing for 16 hours, the resultant mixture is extracted with chloroform. The extract is washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoylacetate as an oily substance. The NMR values of this compound are identical with those of the compound obtained by Reference example 15(1).

Workup

  1. temperatureis refluxed for 5 hours
  2. concentration, The reaction mixture is concentrated under reduced pressure, to the obtained residue
  3. additionis added 20 ml of chloroform and it
  4. washis washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe chloroform is distilled off under reduced pressure and to the residue
  7. additionare added 20 mg of p-toluenesulfonic acid and 20 ml of water
  8. temperatureAfter refluxing for 16 hours
  9. extractionthe resultant mixture is extracted with chloroform
  10. washThe extract is washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee877af79de6461caa86cf2553f0fcab
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Linked notes

Loading…