Water → Allyl (2Z)-3-amino-4-(4-fluorophenyl)-2-butenoate

HRID 458426Notes

Reaction equation

HRID 458426 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:22].O>C1C=CC=CC=1>[NH2:22]/[C:9](/[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[CH:10]\[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 517165Ammonium AcetateHCID 18441988Allyl 4-(4-fluorophenyl)-3-oxobutanoate

Product 1

HCID 86598166Allyl (2Z)-3-amino-4-(4-fluorophenyl)-2-butenoateYield 100.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Allyl 4-(4-fluorophenyl)-3-oxobutanoate (47 g, 198.95 mmol) and ammonium acetate (46.00 g, 596.85 mmol) were refluxed in benzene (250 mL) for 2 h with azeotropic removal of H2O and then cooled and concentrated. The residue was redissolved in Et2O and the organics washed with 1N HCl (2×), H2O, brine, and then dried (Na2SO4), filtered and concentrated to give 47 g (100% yield) of the title compound as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.17 (dd, J=8.4, 5.2 Hz, 2H), 6.99 (t, J=8.6 Hz, 2H), 5.28 (dd, J=17.2, 1.6 Hz, 1H), 5.18 (dd, J=10.3, 1.0 Hz, 1H), 4.61 (s, 1H), 4.55 (d, J=5.6 Hz, 2H), 3.41 (s, 2H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe residue was redissolved in Et2O
  4. washthe organics washed with 1N HCl (2×), H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0753a47f8921476b9677a8022206786a
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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