Triphenylphosphine → HCID 70656902, compound

Into a flask containing 5-(3,4-dichlorophenyl)-1H-pyrazole (1.5 g, 7.04 mmol), (S)-tert-butyl 1-hydroxypropan-2-ylcarbamate (1.357 g, 7.74 mmol) and triphenylphosphine (2.77 g, 10.56 mmol), dry THF (30 ml) was added under nitrogen atmosphere. After few minutes of stirring, DIAD (2.77 ml, 14.08 mmol) was added dropwise through a septum while using icebath to prevent the temperature from rising. The resulting mixture was stirred at RT overnight. The mixture was evaporated. The Boc-protection was removed by adding ethanol (7 ml), 10% HCl/EtOH (50 ml), concentrated HCl (5 ml) and stirring the mixture over the weekend. The mixture was evaporated, extracted with DCM/water. The pH of the water phase was adjusted to ˜12 using 2 M NaOH and extracting the phase again with DCM. The combined organic phases were dried with Na2SO4, filtered and evaporated. 1H-NMR (400 MHz; DMSO-d6): δ 1.00 (d, 3H), 4.70-4.87 (m, 3H), 6.84 (d, 1H), 7.65 (d, 1H), 7.76-7.84 (m, 2H), 8.02 (d, 1H).

1. additionwas added under nitrogen atmosphere
2. stirringThe resulting mixture was stirred at RT overnight
3. customThe mixture was evaporated
4. customThe Boc-protection was removed
5. additionby adding ethanol (7 ml), 10% HCl/EtOH (50 ml), concentrated HCl (5 ml)
6. stirringstirring the mixture over the weekend
7. customThe mixture was evaporated
8. extractionextracted with DCM/water
9. extractionextracting the phase again with DCM
10. dry with materialThe combined organic phases were dried with Na2SO4
11. filtrationfiltered
12. customevaporated

ORD record

ord-fce50b85d7654ec492adf158bf0f4e90

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975254B2