Dimethyl Sulfoxide → HCID 123383739, compound

Temperature

-70 °C

To a solution of oxalylchloride (0.575 mL, 6.5 mmole) in dichloromethane (10 mL) at -70° C., was added dimethylsulfoxide (0.47 mL, 6.5 mmole). The mixture was stirred at -70° C. for 30 minutes before a solution of Compound (1) (2.4 g, 6.2 mmole) in dichloromethane (18 mL) was added. Stirring at -70° C. was continued for 150 minutes. Triethylamine (4.3 mL, 31 mmole) was added dropwise and the reaction mixture was allowed to warm to room temperature over a 20 hour period. The reaction was quenched by the addition of methanol (2 mL), followed 10 minutes later by 60 mL of water. The phases were separated. The aqueous phase was extracted three times with dichloromethane (60 mL each). The combined organic extracts were washed with solutions of dilute hydrochloric acid followed by saturated sodium bicarbonate and brine. After drying the organic extracts over magnesium sulfate, the solvent was removed under reduced pressure to provide 3'-O-[(dimethyl-1,1-dimethylethyl) silyl]-4'-formyl-thymidine (1.88 g) in crude form as a white solid.

1. additionwas added
2. temperatureto warm to room temperature over a 20 hour period
3. customThe reaction was quenched by the addition of methanol (2 mL)
4. waitfollowed 10 minutes later by 60 mL of water
5. customThe phases were separated
6. extractionThe aqueous phase was extracted three times with dichloromethane (60 mL each)
7. washThe combined organic extracts were washed with solutions of dilute hydrochloric acid
8. dry with materialAfter drying the organic extracts over magnesium sulfate
9. customthe solvent was removed under reduced pressure

ORD record

ord-a63df839da2c46f6abe08a4c474e7dd4

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05750343