反应详情

30 Milliliters of anhydrous pyridine and 10 ml of DMF were added to 1.8 g of 4-nitrobenzoic acid, 3.0 g of 6-amidino-1-carbamoylmethyl-2-naphthol.hydrochloride, 2.7 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 DMF. To this collected precipitate was added 100 ml of DMF, 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 to 20 ml under reduced pressure. The residue 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 chloroformmethanol-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 with addition of 20 ml of methanol and 0.6 ml of concentrated hydrochloric acid, and the suspension was added dropwise to a mixed liquid of 200 ml of ether and 20 ml of acetone, followed by stirring for 24 hours under cooling with ice. Then, the precipitate was collected by filtration to obtain 1.35 g of 6-amidino-1-carbamoylmethyl-2-naphthyl 4-nitrobenzoate.hydrochloride.

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 DMF
6. additionTo this collected precipitate was added 100 ml of DMF
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 to 20 ml under reduced pressure
13. additionThe residue was added dropwise to 400 ml of acetone
14. stirringby stirring for 24 hour
15. temperatureunder cooling with ice
16. filtrationThe precipitate was collected by filtration
17. customto obtain a crude product
18. customthe desired fractions were collected
19. distillationthe solvent was distilled off under reduced pressure
20. additionThe residue was suspended with addition of 20 ml of methanol and 0.6 ml of concentrated hydrochloric acid
21. additionthe suspension was added dropwise to a mixed liquid of 200 ml of ether and 20 ml of acetone
22. stirringby stirring for 24 hours
23. temperatureunder cooling with ice
24. filtrationThen, the precipitate was collected by filtration