Water → HCID 68512088, compound

HRID 1717258Notes

Reaction equation

HRID 1717258 reaction equation
[N:1]([C:4]1[CH:16]=[CH:15][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:18]([CH2:25][CH2:26][CH3:27])[CH2:19][C:20]([O:22]CC)=[O:21].[O-]CC.[Na+].O>C(O)C>[CH2:11]([NH:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:1]2[C:18]([CH2:25][CH2:26][CH3:27])=[C:19]([C:20]([OH:22])=[O:21])[N:3]=[N:2]2)=[CH:16][CH:15]=1)=[O:9])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 49787045HCID 49787045, compound

Product 1

HCID 68512088HCID 68512088, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Azido-N-butylbenzamide (2.3 g) obtained in Example 56a) and ethyl 3-oxohexanoate (1.06 ml, 6.33 mmol, 1.25 eq.) were dissolved in ethanol (20 ml), sodium ethoxide (479 mg, 6.33 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 60° C. for 14 hr. Water (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with 2% aqueous sodium carbonate solution (20 ml) and washed with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, washed with ethyl acetate-hexane (1:1, 30 ml), acidified with 6N hydrochloric acid and stood still at 0° C. The precipitate was collected by filtration, washed with ice-cold water and dried to give the title compound as a pale-yellow powder (1.62 g, 4.91 mmol, 97.1%).

Workup

  1. waitat 60° C. for 14 hr
  2. customwas evaporated
  3. additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
  4. washwashed with ethyl acetate-hexane (2:1, 50 ml)
  5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
  6. washwashed with ethyl acetate-hexane (1:1, 30 ml)
  7. customstood still at 0° C
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with ice-cold water
  10. customdried

Sources & evidence

ORD record
ord-fc991e8315454168a0058089f76d4f42
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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