反应详情

Under inert gas, 60 mg of trifluoromethanesulfonic acid 4-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-1-phenylpropylamino]-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-1,4,3-oxathiazin-5-yl}phenyl ester, 5.3 mg of bis(dibenzylideneacetone)palladium and 13.1 mg of 1,2,3,4,5-pentaphenyl-1-(di-tert-butylphosphino)ferrocene were initially charged, dissolved in 1.2 ml of toluene and stirred at room temperature for 5 minutes. After the addition of 0.09 ml of a 2 N solution of trimethylaluminum, the reaction mixture was stirred at 80° C. for 2 hours. After cooling to room temperature, 1 ml of methanol was added and the solvent was removed under reduced pressure. The residue was dissolved in 2 ml of methanol, 0.2 ml of concentrated hydrochloric acid was added and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with 20 ml of ethyl acetate and 10 ml of water, and neutralized with sodium hydroxide solution. The organic phase was washed once again with saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. The product-containing fractions were combined, the acetonitrile was removed under reduced pressure, and the aqueous residue was basified with saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic phase was dried over MgSO4 and concentrated by rotary evaporation, and the residue was taken up again in a mixture of acetonitrile and water and lyophilized. This gave the product (22.8 mg) with a molecular weight of 402.5 g/mol (C21H26N2O4S); MS (ESI): m/e=403 (M+H+).

1. stirringthe reaction mixture was stirred at 80° C. for 2 hours
2. temperatureAfter cooling to room temperature
3. customthe solvent was removed under reduced pressure
4. dissolutionThe residue was dissolved in 2 ml of methanol
5. addition0.2 ml of concentrated hydrochloric acid was added
6. stirringthe mixture was stirred at room temperature for 1 hour
7. additionThe reaction solution was diluted with 20 ml of ethyl acetate and 10 ml of water
8. washThe organic phase was washed once again with saturated aqueous sodium chloride solution
9. dry with materialdried over MgSO4
10. concentrationconcentrated by rotary evaporation
11. customThe residue was purified in a purification laboratory by means of preparative HPLC
12. customthe acetonitrile was removed under reduced pressure
13. extractionextracted with dichloromethane
14. dry with materialThe organic phase was dried over MgSO4
15. concentrationconcentrated by rotary evaporation
16. additionthe residue was taken up again in a mixture of acetonitrile and water