Hydrochloric Acid → Cytidine, 2'-deoxy-5-methyl-, monohydrochloride

Temperature

45 °C

To the suspension of 0.71 g of 3′,5′-O-bis(4-chlorobenzoyl)-5-methyl-2′-deoxycytidine in 4 mL of methanol was added 0.7 mL of the solution of sodium hydroxide in methanol (prepared by dissolving 100 mg of sodium hydroxide in 4 mL of methanol), and the mixture was heated at 45° C. for 5 hours with stirring. After cooling, the mixture was neutralized with a solution of hydrogen chloride in methanol, and methanol was evaporated off. After chloroform and water were added to the residue, the layers were separated, and the aqueous layer was washed with chloroform. The aqueous layer was concentrated and acidified with 6N aqueous hydrogen chloride solution, and after the addition of 5 mL of acetone, allowed to stand overnight at −14° C. The precipitated solid was filtered and dried to give 0.37 g of 5-methyl-2′-deoxycytidine hydrochloride as a light brown solid. Yield 97%.

1. temperatureAfter cooling
2. customwas evaporated off
3. additionAfter chloroform and water were added to the residue
4. customthe layers were separated
5. washthe aqueous layer was washed with chloroform
6. concentrationThe aqueous layer was concentrated
7. additionafter the addition of 5 mL of acetone
8. filtrationThe precipitated solid was filtered
9. customdried

ORD record

ord-3176068583324084bfbb4df18a6d428a

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06822090B2