Triphenylphosphine → {1-[3-Cyano-4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:23][CH2:24][C:25]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[C:30]([C:38]#[N:39])[CH:29]=1)=O)(=[O:22])[CH3:21].C[Si]([N:44]=[N+:45]=[N-:46])(C)C>C1COCC1.CCOC(C)=O>[C:20]([O:23][CH2:24][C:25]1[N:27]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[C:30]([C:38]#[N:39])[CH:29]=2)[N:46]=[N:45][N:44]=1)(=[O:22])[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Triphenylphosphine (2.29 g, 8.73 mmol) and diisopropylazodicorboxylate (1.76 g, 8.70 mmol) were added to a solution of 2-{[3-cyano-4-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate (Intermediate 38, 1.0 g, 3.49 mmol) in THF (20 mL), at 0° C. The reaction mixture was stirred for 30 min at 0° C. and trimethylsilyl azide (1.01 g, 8.77 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature, and then heated to reflux for 4 h. The reaction mixture was diluted with EtOAc and washed with ice water, followed by saturated brine solution. The organic layer was dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 10%-50% EtOAc/pet.ether, to give the title compound (1.5 g, impure).
Workup
- temperatureto warm to room temperature
- temperatureheated
- temperatureto reflux for 4 h
- washwashed with ice water
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
- customto afford the crude compound
- customThis was purified by column chromatography (100-200 mesh silica gel)
- washeluting with 10%-50% EtOAc/pet
Sources & evidence
- ORD record
- ord-7f907fa5a2144041802e78d83d8e4bd1
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115132B2
Reaction notes
Loading…