Benzenepropanoyl chloride → HCID 86640029, compound

HRID 452626Notes

Reaction equation

HRID 452626 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:17]1([CH2:23][CH2:24][C:25](Cl)=[O:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[C:11]([NH:16][C:25](=[O:26])[CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 11492469HCID 11492469, compound

Product 1

HCID 86640029HCID 86640029, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of diethyl[(2-amino-3-pyridyl)methyl]phosphonate (9.65 g, 39.51 mmol) in pyridine (60 mL) was added 3-phenylpropionyl chloride (7.00 mL, 47.41 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 20 hrs. The reaction mixture was concentrated under reduced pressure, a saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-0/1, ethyl acetate/hexane=9/1) to give the title compound (13.56 g, yield 91%) as a brown oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona saturated aqueous sodium hydrogen carbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-0/1, ethyl acetate/hexane=9/1)

Sources & evidence

ORD record
ord-6679df02294b466493364544f9044908
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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