Hydrochloric Acid → 4-Chloro-3-fluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzenesulfonamide

Temperature

0 °C

2-(4-Chloro-3-fluoro-benzenesulfonylamino)-4,4,4-trifluoro-3-trifluoromethyl-butyric acid ethyl ester (150 mg, 0.337 mmol) was dissolved in anhydrous THF (5 mL) and cooled to 0° C. 2M LiBH4 in THF (168 μL in THF) was added and the solution allowed to warm to 25° C. After 18 h, LC-MS revealed unreacted starting ester present. Additional 2M LiBH4 (200 μL) was added and the solution stirred for 24 h. The solution was cooled in an ice bath and 1N hydrochloric acid was added to quench the reaction. The solvent was removed in vacuo and the aqueous phase transferred to a separatory funnel with EtOAc (100 mL) and washed with distilled water (100 mL). The organic layer was removed and the aqueous phase extracted with EtOAc (100 mL×2). The organic extracts were combined, dried (MgSO4), filtered and evaporated to give a white solid (111 mg). This material was purified by Gilson RP-HPLC (column YMC Combiprep 50×20 mm, gradient 10-100% CH3CN: H2O) to afford a white solid (63 mg, 46%). Mass Spectrum (+ESI): 401.8 [M−H]+.

1. temperatureto warm to 25° C
2. temperatureThe solution was cooled in an ice bath
3. customto quench
4. customthe reaction
5. customThe solvent was removed in vacuo
6. customthe aqueous phase transferred to a separatory funnel with EtOAc (100 mL)
7. washwashed with distilled water (100 mL)
8. customThe organic layer was removed
9. extractionthe aqueous phase extracted with EtOAc (100 mL×2)
10. dry with materialdried (MgSO4)
11. filtrationfiltered
12. customevaporated

ORD record

ord-2d67a7dbfc764d90b3b7f9882db3b368

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07550629B2