Water → HCID 68511933, compound
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10](=O)[CH2:11][C:12]([O:14]CC)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]([C:21]1[CH:31]=[CH:30][C:24]([C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=1)=[N+:19]=[N-:20].[O-]CC.[Na+].O>C(O)C>[CH2:28]([NH:27][C:25]([C:24]1[CH:30]=[CH:31][C:21]([N:18]2[C:10]([CH2:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:11]([C:12]([OH:14])=[O:13])[N:20]=[N:19]2)=[CH:22][CH:23]=1)=[O:26])[CH3:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Ethyl 6-phenyl-3-oxohexanoate (1.11 g, 4.73 mmol, 1.25 eq.) obtained in Example 100a) and 4-azido-N-ethylbenzamide (0.719 g, 3.78 mmol) were dissolved in ethanol (20 ml), sodium ethoxide (357 mg, 4.73 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min and at 60° C. for 10.5 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 (1.32 g, 3.50 mmol, 92.6%).
Workup
- customwas evaporated
- additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
- washwashed with ethyl acetate-hexane (2:1, 50 ml)
- extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
- customstood still at 0° C
- filtrationThe precipitate was collected by filtration
- washwashed with ice-cold water
- customdried
Sources & evidence
- ORD record
- ord-4b0e68c234ac4c4b843c7935981ae54f
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07803822B2
Reaction notes
Loading…