Sodium Carbonate → HCID 68515292, compound

HRID 1717295Notes

Reaction equation

HRID 1717295 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH2:10][C:11]([O:13]CC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17]([C:20]1[CH:30]=[CH:29][C:23]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1)=[N+:18]=[N-:19].[O-]CC.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:27]([NH:26][C:24]([C:23]1[CH:29]=[CH:30][C:20]([N:17]2[C:9]([CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:10]([C:11]([OH:13])=[O:12])[N:19]=[N:18]2)=[CH:21][CH:22]=1)=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 61162Ethyl 3-oxo-5-phenylpentanoateHCID 2723922Sodium ethoxideHCID 594322264-azido-N-ethylbenzamide

Product 1

HCID 68515292HCID 68515292, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

Ethyl 5-phenyl-3-oxovalerate (1.27 g, 5.52 mmol, 1.25 eq.) obtained in Example 98a) and 4-azido-N-ethylbenzamide (0.842 g, 4.43 mmol) were dissolved in ethanol (25 ml), sodium ethoxide (417 mg, 5.52 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 80° C. for 3 hr. 2% Aqueous sodium carbonate solution (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with water (20 ml) and washed with ethyl acetate-hexane (2:1, 40 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid and extracted with ethyl acetate (35 ml×2). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether-ethyl acetate (2:1, about 8 ml) was added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a pale-brown powder (1.56 g, 4.27 mmol, 96.4%).

Workup

  1. customwas evaporated
  2. additionthe residue was diluted with water (20 ml)
  3. washwashed with ethyl acetate-hexane (2:1, 40 ml)
  4. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
  5. extractionextracted with ethyl acetate (35 ml×2)
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. additiondiethyl ether-ethyl acetate (2:1, about 8 ml) was added
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-e36ca21e427f4749b988afc1c972c544
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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