反应详情

40 Milliliters of 20% hydrous pyridine was added to 3.0 g of 4-dimethylaminobenzoic acid, 1.77 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 2.65 g of DCC and 130.9 mg of DMAP, followed by stirring for 2 hours under cooling with ice and then 24 hours at room temperature. Then, the precipitate was collected by filtration and washed with a small amount of pyridine. To this collected precipitate were added 60 ml of DMF and 20 ml of water to dissolve the precipitate with heating, followed by stirring for 2 hours under cooling with ice. Then, insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. To the residue were added 15 ml of DMF and 10 ml of water to dissolve the residue. The solution was added dropwise to 400 ml of acetone, followed by stirring for 24 hour under cooling with ice. The precipitate was collected by filtration to obtain a crude product. Then, the product was subjected to silica gel column chromatography using methyl ethyl ketone-water-acetic acid (80:15:5) as an eluent, and the desired fractions were collected and the solvent was distilled off under reduced pressure. The residue was suspended in 15 ml of methanol, 5 ml of DMF and 0.9 ml of concentrated hydrochloric acid, and the suspension was added dropwise to a mixed liquid of 200 ml of acetone and 100 ml of ether, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 1.96 g of the desired product.

1. temperatureunder cooling with ice
2. custom24 hours
3. customat room temperature
4. filtrationThen, the precipitate was collected by filtration
5. washwashed with a small amount of pyridine
6. additionTo this collected precipitate were added 60 ml of DMF and 20 ml of water
7. dissolutionto dissolve the precipitate
8. temperaturewith heating
9. stirringby stirring for 2 hours
10. temperatureunder cooling with ice
11. filtrationThen, insoluble matter was filtered off
12. concentrationthe filtrate was concentrated under reduced pressure
13. additionTo the residue were added 15 ml of DMF and 10 ml of water
14. dissolutionto dissolve the residue
15. additionThe solution was added dropwise to 400 ml of acetone
16. stirringby stirring for 24 hour
17. temperatureunder cooling with ice
18. filtrationThe precipitate was collected by filtration
19. customto obtain a crude product
20. customthe desired fractions were collected
21. distillationthe solvent was distilled off under reduced pressure
22. addition5 ml of DMF and 0.9 ml of concentrated hydrochloric acid, and the suspension was added dropwise to a mixed liquid of 200 ml of acetone and 100 ml of ether
23. stirringby stirring for 24 hours
24. temperatureunder cooling with ice
25. filtrationThen, the precipitate was collected by filtration