Uracil → 3,5-Dioxohexanoic acid

N,O-Bis(trimethylsilyl)acetamide (BSA, 54.7 mL, 224 mmol) was added to a stirred suspension of uracil (10.2 g, 90.7 mmol) and Compound 54 (31.1 g, 60.4 mmoles) in dry acetonitrile (300 mL). After stirring at rt for 30 min a clear solution was observed, and the reaction was cooled to 0° C. under nitrogen. Trimethylsilyfluoromethanesulfonate (TMSOTf, 21.9 mL, 121 mmol) was added and after the reaction was stirred at rt for 15 min, it was transferred to a preheated oil bath at 80° C. After stirring for 4 h at 80° C., the reaction was cooled to rt and MeO H (20 mL), EtOAc (250 mL) and H2O (400 mL) were added. The organic phase was then sequentially washed with sat. NaHCO3, brine, dried (Na2SO4) and concentrated to provide the crude triacetate. TLC (Rf═0.60, 80% EtOAc/hexanes). LCMS (Method m/z═567.1 (M+H).

1. temperaturethe reaction was cooled to 0° C. under nitrogen
2. stirringafter the reaction was stirred at rt for 15 min
3. customit was transferred to a preheated oil bath at 80° C
4. stirringAfter stirring for 4 h at 80° C.
5. temperaturethe reaction was cooled to rt
6. washThe organic phase was then sequentially washed with sat. NaHCO3, brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated

ORD record

ord-a8617aaaf81e43a8aaa35b1780aca161

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993738B2