(Trifluoromethyl)trimethylsilane → 5-Chloro-n-[(s,s)-2-methyl-1-(2,2,2-trifluoro-1-hydroxyethyl)butyl]thiophene-2-sulfonamide

Temperature

25 °C

To a 0° C. solution of 5-chlorothiophene-2-sulfonyl isoleucinal (770 mg, 2.6 mmol, see Example 118, parts 1&2) in THF (5 mL) was added TMS-CF3 (5 mL, 0.5M in THF). The resulting mixture was treated with TBAF (250 μL, 1M in THF). The cold bath was removed and the reaction was stirred at 25° C. overnight. The reaction was quenched with HCl (25 mL, 2M) and the resulting solution was extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with water (25 mL) and brine (25 mL) then dried over MgSO4. The residue was submitted to RP-HPLC (see example 155 for procedure) to give 74 mg of the desired product (m/z=364.0 (M−H), rt=1.23 min).

1. customThe cold bath was removed
2. customThe reaction was quenched with HCl (25 mL, 2M)
3. extractionthe resulting solution was extracted with ethyl acetate (3×15 mL)
4. washThe combined organic extracts were washed with water (25 mL) and brine (25 mL)
5. dry with materialthen dried over MgSO4

ORD record

ord-4b29faaefd2347daac0acad1f9ceb1aa

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691884B2