Dicyclohexylcarbodiimide → HCID 178520712, compound

Temperature

0 °C

To a cool (0° C.), stirred suspension of furan-2,4(3H,5H)-dione (16.46 g, 164 mmol) in DCM (650 mL) was added TEA (23.0 mL, 165 mmol), DMAP (6.04 g, 49.4 mmol), 3,3,3-trifluoropropanoic acid (16.0 mL, 181 mmol) and DCC (40.70 g, 197 mmol) resulting in a yellow homogenous solution. The solution was stirred at 0° C., and then was allowed to warm to room temperature as the bath warmed while stirring overnight. The suspension was filtered and the solid was washed with DCM. The deep red filtrate was concentrated under reduced pressure. The residue was partitioned between EtOAc and 1M HCl (400 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to afford an amber solid. This was dissolved in a minimum amount of CH3CN, to which DCM was added to form a precipitate. The suspension was allowed to stand in the freezer overnight. It was sonicated then cooled and filtered, the solid was washed with cold DCM and then dried to provide Preparation 1A (31.62 g, 91%) as a cream solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 13.07 (1H, br. s.), 4.29 (2H, s), 3.80 (2H, q, J=11.67 Hz).

1. customresulting in a yellow homogenous solution
2. stirringThe solution was stirred at 0° C.
3. temperatureto warm to room temperature as the bath
4. temperaturewarmed
5. stirringwhile stirring overnight
6. filtrationThe suspension was filtered
7. washthe solid was washed with DCM
8. concentrationThe deep red filtrate was concentrated under reduced pressure
9. customThe residue was partitioned between EtOAc and 1M HCl (400 mL)
10. washThe organic phase was washed with brine
11. dry with materialdried (Na2SO4)
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customto afford an amber solid
15. additionwas added
16. customto form a precipitate
17. customto stand in the freezer overnight
18. customIt was sonicated
19. temperaturethen cooled
20. filtrationfiltered
21. washthe solid was washed with cold DCM
22. customdried
23. customto provide

ORD record

ord-6e63b7985fc2489e967bc0718f428928

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133139B2