Sodium Hydroxide → HCID 68514256, compound

HRID 1717313Notes

Reaction equation

HRID 1717313 reaction equation
[F:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=O)[CH2:7][C:8]([O:10]CC)=[O:9].[N:14]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)=[N+:15]=[N-:16].[O-]CC.[Na+].[OH-].[Na+]>C(O)C.O>[CH2:24]([NH:23][C:21]([C:20]1[CH:26]=[CH:27][C:17]([N:14]2[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][F:1])=[C:7]([C:8]([OH:10])=[O:9])[N:16]=[N:15]2)=[CH:18][CH:19]=1)=[O:22])[CH3:25]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 2723922Sodium ethoxideHCID 594322264-azido-N-ethylbenzamideHCID 86629803HCID 86629803, compound

Product 1

HCID 68514256HCID 68514256, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Ethyl 7-fluoro-3-oxoheptanoate (0.920 g, 4.84 mmol, 1.17 eq.) obtained in Example 108a) and 4-azido-N-ethylbenzamide (0.790 g, 4.15 mmol) were dissolved in ethanol (25 ml), sodium ethoxide (366 mg, 4.84 mmol, 1.17 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 60° C. for 11 hr. 1N Aqueous sodium hydroxide solution (4.15 ml, 1.0 eq.) was added to the reaction mixture and the mixture was further stirred for 1 hr. Water (20 ml) was added to the reaction mixture, ethanol was evaporated, and washed with ethyl acetate-hexane (1:1, 50 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, and acidified (pH<3) with 6N hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to give the title compound as a pale-gray powder (1.26 g, 3.77 mmol, 90.8%).

Workup

  1. waitat 60° C. for 11 hr
  2. stirringthe mixture was further stirred for 1 hr
  3. customwas evaporated
  4. washwashed with ethyl acetate-hexane (1:1, 50 ml)
  5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-56383ad67d6c4908b606579e5036ec34
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…