Water → HCID 68514388, compound

HRID 1717301Notes

Reaction equation

HRID 1717301 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=O)[CH2:13][C:14]([O:16]CC)=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20]([C:23]1[CH:33]=[CH:32][C:26]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1)=[N+:21]=[N-:22].[O-]CC.[Na+].O>C(O)C>[CH2:30]([NH:29][C:27]([C:26]1[CH:32]=[CH:33][C:23]([N:20]2[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:13]([C:14]([OH:16])=[O:15])[N:22]=[N:21]2)=[CH:24][CH:25]=1)=[O:28])[CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 54503892HCID 54503892, compoundHCID 594322264-azido-N-ethylbenzamide

Product 1

HCID 68514388HCID 68514388, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Ethyl 8-phenyl-3-oxooctanoate (1.01 g, 3.84 mmol, 1.23 eq.) obtained in Example 101a) and 4-azido-N-ethylbenzamide (purity 95%, 0.624 g, 3.12 mmol) were dissolved in ethanol (20 ml), sodium ethoxide (290 mg, 3.84 mmol, 1.23 eq.) was added, and the mixture was stirred at room temperature for 30 min and 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, acidified (pH<3) 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 (1.26 g, 3.10 mmol, 99.5%).

Workup

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

Sources & evidence

ORD record
ord-155b1a463c754234a26e8e26835eaf65
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

Loading…