Sodium Carbonate → HCID 178432547, compound

HRID 1878081Notes

Reaction equation

HRID 1878081 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[NH:9])=[N:6][CH:7]=1.[CH2:11]([CH:18]([C:24](=O)[CH3:25])[C:19](OCC)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:10]=[C:19]([OH:20])[C:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:24]([CH3:25])[N:9]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 246929Ethyl alpha-benzylacetoacetateHCID 55289624HCID 55289624, compound

Product 1

HCID 178432547HCID 178432547, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound of example 12 (0.2 g, 1.47 mmol) in water (5 mL) and ethanol (2.5 mL) was added ethyl 2-benzyl-3-oxobutanoate(0.379 g, 2.35 mmol) and sodium carbonate (0.280 g, 2.64 mmol) at room temperature, and the reaction mixture was stirred for about 24 hours. Ethanol was removed under reduced pressure, and the reaction mixture was diluted with water and extracted with ethyl acetate (3×20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was purified by column chromatography using silica gel and 1% methanol in chloroform as an eluent to obtain the title compound.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionthe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the crude product, which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-79ba5d1315d644f69e631167a2ab9bab
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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