Water → {4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16](OC(=O)C(F)(F)F)[C:17]2[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=2[Cl:23])=[C:11]([N+:33]([O-:35])=[O:34])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]2[C:18]([O:24][CH3:25])=[N:19][CH:20]=[CH:21][C:22]=2[Cl:23])=[C:11]([N+:33]([O-:35])=[O:34])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of trifluoro-acetic acid 2-(4-tert-butoxycarbonylamino-2-nitro-phenyl)-1-(4-chloro-2-methoxy-pyridin-3-yl)-ethyl ester (crude 1.60 g, 3.08 mmol) in THF (10 mL) was added 8-diazabicyclo[5.4.0]undec-7-ene (1.33 g, 8,74 mmol) at 25° C. The reaction was allowed to stir at 70° C. for 3 hours. The reaction mixture was cooled to 25° C., and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (80/20 hexanes/ethyl acetate) afforded {4-[(E)-2-(4-chloro-2-methoxy-pyridin-3-yl)-vinyl]-3-nitro-phenyl}-carbamic acid tert-butyl ester (800 mg, 68%) as an oil. MH+ 406.0.
Workup
- temperatureThe reaction mixture was cooled to 25° C.
- extractionThe aqueous phase was extracted three times with ethyl acetate
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationFiltration
- concentrationfollowed by concentration in vacuo
- customgave a brown solid
Sources & evidence
- ORD record
- ord-929b11c3fe034904b4b83a5f1c6dc8b0
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388166B2
Reaction notes
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