Benzoyl chloride → HCID 178522338, compound

Temperature

0 °C

A suspension of 1.22 g (5.02 mmol) of cytosine-β-D-arabinofuranoside in 50 mL of dry pyridine was cooled to 0° C. 10 mL of benzoyl chloride was added and the mixture was stirred at room temperature for 16 hours. The mixture was poured into 75 mL of 5% aq sodium bicarbonate solution and extracted with CH2CL2 (2×150 mL). The organic phases were washed with water (50 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The mixture was dissolved in 50 mL of pyridine/methanol/water (5:3:2 v/v) and cooled in an ice bath. To this solution was added cold 50 mL of 2M sodium hydroxide in pyridine/methanol/water (5:3:2 v/v). The reaction mixture was stirred at 0° C. for 15 minutes and then the pH was adjusted to 7 with the addition of ammonium chloride. The mixture was concentrated in vacuo and 20 mL of methanol was added. The mixture was filtered and the solid washed with more methanol (3×20 mL). All washings and filtrate were collected, combined and concentrated in vacuo. Redissolved in 50 mL of methanol/CH2Cl2 (2:8 v/v) and the mixture was purified by flash chromatography using methanol/CH2Cl2 (1:9-2:8 v/v). A second flash chromatography as described above was needed to remove all impurities to give 1.5 g (86%) of N4-Benzoylcytosine-β-D-arabinofuranoside 16.

1. extractionextracted with CH2CL2 (2×150 mL)
2. washThe organic phases were washed with water (50 mL)
3. dry with materialdried over anhydrous MgSO4
4. concentrationconcentrated in vacuo
5. dissolutionThe mixture was dissolved in 50 mL of pyridine/methanol/water (5:3:2 v/v)
6. temperaturecooled in an ice bath
7. additionTo this solution was added cold 50 mL of 2M sodium hydroxide in pyridine/methanol/water (5:3:2 v/v)
8. stirringThe reaction mixture was stirred at 0° C. for 15 minutes
9. additionthe pH was adjusted to 7 with the addition of ammonium chloride
10. concentrationThe mixture was concentrated in vacuo and 20 mL of methanol
11. additionwas added
12. filtrationThe mixture was filtered
13. washthe solid washed with more methanol (3×20 mL)
14. customAll washings and filtrate were collected
15. concentrationconcentrated in vacuo
16. dissolutionRedissolved in 50 mL of methanol/CH2Cl2 (2:8 v/v)
17. customthe mixture was purified by flash chromatography
18. customto remove all impurities

ORD record

ord-9a142b18630945d5b4332d3fd8fb348c

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06258360B1