反应详情

2-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (1.20 g) was added to a mixture of dichloromethane and saturated aqueous sodium hydrogencarbonate, and was extracted with dichloromethane. The separated organic layer was washed with water, and brine, and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and resulting residue was dissolved in dimethylformamide (25 ml). To the reaction mixture was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.71 g) and 3-(tert-butyloxycarbonyl)-4-thiazolidinylcarboxylic acid (0.77 g), and stirred at ambient temperature for 2 hours. The mixture was poured into water, and extracted with ethyl acetate. The separated organic layer was washed with saturated aqueous sodium hydrogencarbonate, water, and brine, and dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The residue was subjected to column chromatography on silica gel (50 g) and eluted with a mixture of methanol and chloroform. The fractions containing the object compound were combined and evaporated in vacuo. The resulting residue (oil-compound) (1.10 g) was dissolved with dichloromethane (20 ml), and stirred at 2° C. To the reaction mixture was added 1,4-dioxan solution of 4N hydrogen chloride (10 ml), and stirred at ambient temperature for 1 hour. The resulting residue was evaporated in vacuo. The residue was added iso-propyl ether (50 ml) and stirred at 2° C. for 3 hours. The resulting precipitate was collected by filtration and washed with iso-propyl ether, to give 4-methoxyphenyl)-2-(4-thiazolidinylcarbonylaminomethyl)thiazole hydrochloride (0.45 g).

1. extractionwas extracted with dichloromethane
2. washThe separated organic layer was washed with water, and brine
3. dry with materialdried over magnesium sulfate
4. filtrationAfter filtration
5. customthe filtrate was evaporated in vacuo
6. customresulting residue
7. extractionextracted with ethyl acetate
8. washThe separated organic layer was washed with saturated aqueous sodium hydrogencarbonate, water, and brine
9. dry with materialdried over magnesium sulfate
10. additiontreated with activated charcoal
11. filtrationAfter filtration
12. customthe filtrate was evaporated in vacuo
13. washeluted with a mixture of methanol and chloroform
14. additionThe fractions containing the object compound
15. customevaporated in vacuo
16. dissolutionThe resulting residue (oil-compound) (1.10 g) was dissolved with dichloromethane (20 ml)
17. stirringstirred at 2° C
18. additionTo the reaction mixture was added 1,4-dioxan solution of 4N hydrogen chloride (10 ml)
19. stirringstirred at ambient temperature for 1 hour
20. customThe resulting residue was evaporated in vacuo
21. additionThe residue was added iso-propyl ether (50 ml)
22. stirringstirred at 2° C. for 3 hours
23. filtrationThe resulting precipitate was collected by filtration
24. washwashed with iso-propyl ether