Methanol → HCID 54112621, compound

Temperature

0 °C

In a nitrogen atmosphere, 3.0 mL of a methylene chloride solution 1 mol/L boron trichloride was added to a solution of 70 mg of (3S,4S,5R)-2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-fluoro-4-((4-methylbenzyl)oxy)-5-(((4-methylbenzyl)oxy)methyl)thiolane in 4.6 mL of methylene chloride under cooling on dry ice/acetone, and the obtained mixture was then stirred at the same temperature as described above for 3.5 hours. Thereafter, the temperature of the reaction mixture was increased to 0° C., and the mixture was then stirred for 30 minutes. Thereafter, 3.0 mL of methanol was added to the reaction mixture, and the thus obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, a solid was then collected by filtration, and it was then purified by silica gel column chromatography (chloroform/methanol=100/0 to 60/40), so as to obtain 63 mg of (2R,3S,4S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-fluoro-2-(hydroxymethyl)thiolan-3-ol in the form of a white solid.

1. temperatureunder cooling on dry ice/acetone
2. customas described above for 3.5 hours
3. stirringthe mixture was then stirred for 30 minutes
4. stirringthe thus obtained mixture was then stirred at room temperature for 30 minutes
5. filtrationThereafter, a solid was then collected by filtration, and it
6. customwas then purified by silica gel column chromatography (chloroform/methanol=100/0 to 60/40)

ORD record

ord-2b2ff973710d42c2a423a49d07d707bf

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221865B2