Trifluoroacetic acid → HCID 58238609, compound

Temperature

5 °C

At 0° C. triethylsilane (1.09 g, 9.4 mmol, 1.3 equiv) was added to compound 7 (2.0 g, 7.2 mmol, 1.0 equiv) in dichloromethane (50 mL). Trifluoroacetic acid (4.1 g, 36.1 mmol, 5.0 equiv) was added dropwise while maintaining the temperature<5° C. The reaction was allowed to warm to room temperature at which point the solution became a yellowish-green color. The reaction was stirred for 96 hr, LC/MS and TLC indicated the reaction was incomplete. The reaction was then refluxed for an additional 18 hr, at this point LC/MS and TLC indicated the reaction was complete. The reaction was carefully quenched with saturated sodium bicarbonate (100 mL). The layers were separated, the organic layer was dried over sodium sulfate and absorbed onto silica gel (5 g) by concentration under reduced pressure. This material was purified on a silica gel column (30 g) by eluting with heptanes (150 mL), ethyl acetate (2%) in heptanes (200 mL) and ethyl acetate (5%) in heptanes (200 mL). The desired product was isolated pure in nearly 70% yield (1.3 g).

1. temperatureto warm to room temperature at which point the solution
2. temperatureThe reaction was then refluxed for an additional 18 hr, at this point LC/MS and TLC
3. customThe reaction was carefully quenched with saturated sodium bicarbonate (100 mL)
4. customThe layers were separated
5. dry with materialthe organic layer was dried over sodium sulfate
6. customabsorbed onto silica gel (5 g) by concentration under reduced pressure
7. customThis material was purified on a silica gel column (30 g)
8. washby eluting with heptanes (150 mL), ethyl acetate (2%) in heptanes (200 mL) and ethyl acetate (5%) in heptanes (200 mL)

ORD record

ord-704b5188846d41f8b8e761f2c4a2e813

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546501B2