反应详情

6-(3-Chloro-4-fluorobenzyl)-1-[(dimethylamino)carbonyl]-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-3,4-diyl diacetate (30 g, 62.7 mmol) was dissolved in 500 mL MeOH and treated with a 30% by weight solution of NaOMe in MeOH (45.2 mL, 251 mmol 4 equivalents was sufficient to get the pH of the reaction to 9) for 1 hour at 40° C. LCMS showed the cleavage of the acetate groups was complete. The reaction was neutralized with 1N HCl and the volume reduced to remove the MeOH and the residue was diluted with water and acidified to pH 3. The cloudy aqueous layer was diluted with an equal volume (800 mL) of chloroform. After shaking, the product began to crystallize out of the solutions and gathered at the miniscus. The total contents of the funnel were filtered and the collected solids were washed with water until no more salts appeared to remain. The solid was dried in vacuo for 16 hours to give a cinnamon colored solid. The organic layer from the filtered extraction was collected, washed with water and dried over Na2SO4, filtered and evaporated. The residue was crystallized from methanol to give product. The crude material was quite insoluble but was crystallized from DMF, then boiled in MeOH, filtered and dried under vacuum to give product.

1. customto get
2. customthe pH of the reaction to 9) for 1 hour at 40° C
3. customto remove the MeOH
4. additionthe residue was diluted with water
5. additionThe cloudy aqueous layer was diluted with an equal volume (800 mL) of chloroform
6. customto crystallize out of the solutions
7. filtrationThe total contents of the funnel were filtered
8. washthe collected solids were washed with water until no more salts
9. customThe solid was dried in vacuo for 16 hours
10. customto give a cinnamon
11. extractionThe organic layer from the filtered extraction
12. customwas collected
13. washwashed with water
14. dry with materialdried over Na2SO4
15. filtrationfiltered
16. customevaporated
17. customThe residue was crystallized from methanol
18. customto give product
19. customwas crystallized from DMF
20. filtrationfiltered
21. customdried under vacuum
22. customto give product