反应详情

A mixture, cooled to 0° C., of N-[(S)-6-(1-hydroxy-1-methylethyl)-1,2,3,4-tetrahydronaphthalen-2-yl]-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.30 g), glacial acetic acid (1 ml) and trimethylsilyl cyanide (145 mg) was admixed dropwise with sulfuric acid (1.2 ml; 96%). The cooling bath was removed and the mixture was stirred for another 12 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with sodium chloride solution, dried over sodium sulfate and concentrated. The residue was taken up in 1,4-dioxane (20 ml) and boiled at reflux with dilute hydrochloric acid for 30 minutes. The reaction mixture was washed with ethyl acetate and basified with concentrated sodium hydroxide solution. Extraction with dichloromethane gave rise to an organic phase which was dried over sodium sulfate and concentrated. (Alternatively, the hydrolysis of the intermediate formamide can also be achieved by boiling with sodium hydroxide solution.) The product was thus obtained with the molecular weight of 408.55 (C25H32N2O3); MS (ESI): 409 (M+H+).

1. customThe cooling bath was removed
2. additionThe reaction mixture was diluted with water
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with sodium chloride solution
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated
7. temperatureat reflux with dilute hydrochloric acid for 30 minutes
8. washThe reaction mixture was washed with ethyl acetate and basified with concentrated sodium hydroxide solution
9. extractionExtraction with dichloromethane
10. customgave rise to an organic phase which
11. dry with materialwas dried over sodium sulfate
12. concentrationconcentrated
13. custom(Alternatively, the hydrolysis of the intermediate formamide
14. custom) The product was thus obtained with the molecular weight of 408.55 (C25H32N2O3)