Potassium Carbonate → HCID 131729387, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of {(3R,4S,5S)-5-[3-fluoro-4-nitro-5-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-benzyl]-4-hydroxy-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester (3.31 g, 6.0 mmol) in THF-H2O 1:1 (150 mL) was added oxone (7.6 g, 12.0 mmol). After stirring the reaction mixture for 2 h at 25° C., 2.5 g NaOAc and 3 g sodium metabisulfite were added. The reaction mixture was stirred for 0.5 h, basified with saturated aq. K2CO3-solution and the product was extracted with EtOAc. Combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound after chromatographic purification (Combi-Flash, 40 g silicagel, hexane-EtOAc 95:5 to EtOAc) as a colorless amorphous solid: TLC (toluene-THF 1:1) Rf=0.45; HPLC RtA=2.21 min; ESIMS [M+NH4]+=602; 1H NMR (400 MHz, CDCl3): δ 6.92 (d, 1H), 6.85 (s, 1H), 5.05 (m, 1H), 4.92 (d, 1H), 4.02 (m, 1H), 3.45 (m, 1H), 3.34 (m, 2H), 3.22 (dd, 1H), 3.18 (m, 1H), 2.94 (m, 1H), 2.82 (dd, 1H), 2.74 (dd, 1H), 2.52 (m, 1H), 1.43 (s, 9H).

Provenance & Evidence