反应详情

A solution of 1-bromo-4-(chloro(isocyanato)methyl)benzene (1.07 g, 4.34 mmol) in dichloromethane (5 mL) is added to a solution of 5-oxo-3-(3-(trifluoromethyl)phenyl-amino)cyclohex-3-enecarboxylic acid (intermediate 22, 1.30 g, 4.34 mmol) in dichloromethane (15 mL) and the mixture is heated at reflux for 3 h. Water and aqueous sodium hydroxide solution are added and the mixture is washed with diethyl ether. The organic layer is discarded and the aqueous layer is acidified with aqueous hydrogen chloride and extracted twice with diethyl ether. The organic layers are combined, dried over Na2SO4 and concentrated under reduced pressure. Yield: 770 mg; ESI mass spectrum: [(79Br)-M+H]+=509, [(81Br)-M+H]+=511; Retention time HPLC: 1.25 min, 1.35 min (1:1 mixture of diastereomers) (V001—006).

1. temperaturethe mixture is heated
2. temperatureat reflux for 3 h
3. washthe mixture is washed with diethyl ether
4. extractionextracted twice with diethyl ether
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. additionRetention time HPLC: 1.25 min, 1.35 min (1:1 mixture of diastereomers) (V001—006)