Hydrochloric Acid → HCID 86688426, compound

To a solution of (S)-N-((R)-1 (4-chloro-2-(trifluoromethyl)phenyl)ethyl)-2-methylpropane-2-sulfinamide (14.6 g, 44.5 mmol) in methanol (25 mL) was added a solution of hydrochloric acid in p-dioxane (4.0 M in p-dioxane, 22.3 mL, 89.1 mmol), and the reaction was stirred at room temperature for 30 min. Diethyl ether was then added (400 mL) and the slurry was stirred for 10 min. The solid was collected by filtration, and washed with diethyl ether (2×200 mL). The solid was then dissolved in 5 M aqueous sodium hydroxide solution, and extracted with dichloromethane (2×100 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was used without further purification (7.8 g, 34.9 mmol, 79%, >96% ee, determined by Mosher's method).

1. stirringthe slurry was stirred for 10 min
2. filtrationThe solid was collected by filtration
3. washwashed with diethyl ether (2×200 mL)
4. dissolutionThe solid was then dissolved in 5 M aqueous sodium hydroxide solution
5. extractionextracted with dichloromethane (2×100 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was used without further purification (7.8 g, 34.9 mmol, 79%, >96% ee, determined by Mosher's method)

ORD record

ord-6500b53931004fa787306cb49ea3aa2c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685959B2