Ammonium Acetate → HCID 69075956, compound

HRID 1182600Notes

Reaction equation

HRID 1182600 reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:9][O:10][C:11](=[O:16])[CH2:12]C(C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([O-])(=O)[CH3:24].[NH4+:27].[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:41](=[O:55])[C:42]([C:52](=O)[CH3:53])=[CH:43][C:44]2[CH:49]=[C:48]([Cl:50])[CH:47]=[C:46]([Cl:51])[CH:45]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>CC(O)C>[C:28]([O:32][C:33]([N:35]1[CH2:36][CH2:37][N:38]([C:41]([C:42]2[CH:43]([C:44]3[CH:49]=[C:48]([Cl:50])[CH:47]=[C:46]([Cl:51])[CH:45]=3)[C:12]([C:11]([O:10][CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])=[C:23]([CH3:24])[NH:27][C:52]=2[CH3:53])=[O:55])[CH2:39][CH2:40]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 17825670HCID 17825670, compoundHCID 86590786HCID 86590786, compound

Product 1

HCID 69075956HCID 69075956, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

355 mg (1.20 mmol) of acetoacetic acid 3,3-diphenylpropyl ester and 277 mg (3.59 mmol) of ammonium acetate were stirred in 15 ml of 2-propanol at 55° C. overnight. After evaporating 2-propanol under reduced pressure, ethyl acetate was added and the reaction mixture was washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained substance was dissolved in 15 ml of 2-propanol. 513 mg (1.20 mmol) of 4-[2-acetyl-3-(3,5-dichlorophenyl)-2-propenoyl] piperazine-1-carboxylic acid-t-butyl ester was added and stirred at 70° C. overnight. After evaporating 2-propanol under reduced pressure, the residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 50/1) to obtain the title compound.

Workup

  1. customAfter evaporating 2-propanol under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe reaction mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe obtained substance was dissolved in 15 ml of 2-propanol
  7. customAfter evaporating 2-propanol under reduced pressure
  8. customthe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1 to 50/1)

Sources & evidence

ORD record
ord-71a412e28fea4b40a0b4656e1d5cb86a
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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