Ammonium Acetate → Bis(1,1-Dimethylethyl) 2-[(1Z)-1-amino-3-(ethyloxy)-3-oxo-1-propen-1-yl]-1,4-piperazinedicarboxylate

HRID 1427152Notes

Reaction equation

HRID 1427152 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]([CH:8]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O)[CH3:2].C([O-])(=O)C.[NH4+:33]>C(O)C>[NH2:33]/[C:6](/[CH:8]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:11][CH2:10][N:9]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])=[CH:5]\[C:4]([O:3][CH2:1][CH3:2])=[O:28]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 70559668Bis(1,1-Dimethylethyl) 2-[3-(ethyloxy)-3-oxopropanoyl]-1,4-piperazinedicarboxylate2×

Product 1

HCID 70556570Bis(1,1-Dimethylethyl) 2-[(1Z)-1-amino-3-(ethyloxy)-3-oxo-1-propen-1-yl]-1,4-piperazinedicarboxylateYield 103%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of bis(1,1-dimethylethyl) 2-[3-(ethyloxy)-3-oxopropanoyl]-1,4-piperazinedicarboxylate (may be prepared as described in Intermediate 3; 7.2 g) in ethanol (250 mL) was added ammonium acetate (6.93 g). The reaction mixture was heated to reflux for 7 hours and then left to stand at room temperature overnight. The reaction mixture was evaporated and then partitioned between 2× EtOAc and water. The combined organic phases were washed with water, dried through a hydrophobic frit and evaporated to give the title compound as a yellow oil (7.40 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 hours
  3. waitleft
  4. customThe reaction mixture was evaporated
  5. custompartitioned between 2× EtOAc and water
  6. washThe combined organic phases were washed with water
  7. customdried through a hydrophobic frit
  8. customevaporated

Sources & evidence

ORD record
ord-5ee08bc0f5d04699860b3e2b463f1df9
Source dataset
uspto-grants-2015_01
Patent number
US08933132B2

Reaction notes

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