Potassium Carbonate → [(3R*,4S*,5S*)-5-(3,5-Difluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of [(3R,4S,5S)-5-(3,5-difluoro-4-nitro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester (2.05 g, 4.9 mmol) in THF-water 1:1 (60 mL) was added oxone (6.52 g, 10.3 mmol). After stirring the reaction mixture for 2 h at 40° C., 2 g NaOAc and 2 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 crystallization from THF-hexane as yellow crystals: TLC (hexane-THF 1:1) Rf=0.23; HPLC RtA=1.76 min; ESIMS [M+NH4]+=454; 1H NMR (600 MHz, DMSO-d6): δ 7.32 (d, 2H), 6.91 (d, 1H), 3.73 (m, 1H), 3.0-3.2 (m, 5H), 2.94 (m, 1H), 2.74 (dd, 1H), 2.18 (m, 1H), 1.38 (s, 9H).

Provenance & Evidence