Water → HCID 68513197, compound

HRID 1717263Notes

Reaction equation

HRID 1717263 reaction equation
[N:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O=[C:21]([CH2:28][CH2:29][CH3:30])[CH2:22][C:23]([O:25]CC)=[O:24].[O-]CC.[Na+].O>C(O)C>[CH2:11]([NH:10][C:8]([C:7]1[CH:18]=[CH:19][C:4]([N:1]2[C:21]([CH2:28][CH2:29][CH3:30])=[C:22]([C:23]([OH:25])=[O:24])[N:3]=[N:2]2)=[CH:5][CH:6]=1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 238498Ethyl 3-oxohexanoateHCID 2723922Sodium ethoxideHCID 86629796HCID 86629796, compound

Product 1

HCID 68513197HCID 68513197, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Azido-N-benzylbenzamide obtained in Example 58a) and ethyl 3-oxohexanoate (1.08 ml, 6.44 mmol, 1.25 eq.) were dissolved in ethanol (20 ml), sodium ethoxide (487 mg, 6.44 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 10 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 grayish white powder (1.71 g, 4.70 mmol, 91.3%).

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-af2946d12c204f339aa655f4dd2d82e1
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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