反应详情

To a solution of {(3R,4S,5S)-5-[4-Nitro-3-fluoro-5-(2,2,2-trifluoro-ethoxy)-benzyl]-4-hydroxy-tetrahydro-thiopyran-3-yl}-carbamic acid tert-butyl ester (1.5 g, 3.1 mmol) in THF (20 mL) and water (12 mL) at 0° C. was added oxone (5.71 g, 9.3 mmol) in portions. After 2 h excess oxone was destroyed with sodiummetabisulfite. The reaction mixture was diluted with EtOAc (200 mL) and washed with aqueous saturated bicarbonate solution and brine. The organic phase was dried with Na2SO4, filtered and evaporated to provide a beige powder: TLC (cyclohexane-EtOAc 1:1) Rf=0.12; ESIMS [M+NH4]+=534; 1H NMR (600 MHz, DMSO-d6): δ 7.10 (m, 2H), 6.89 (d, 1H), 5.25 (d, 1H), 5.01-4.94 (m, 2H), 3.70 (m, 1H), 3.20-3.00 (m, 5H), 2.93 (m, 1H), 2.68 (m, 1H), 2.17 (m, 1H), 1.38 (s, 9H).

1. customAfter 2 h excess oxone was destroyed with sodiummetabisulfite
2. additionThe reaction mixture was diluted with EtOAc (200 mL)
3. washwashed with aqueous saturated bicarbonate solution and brine
4. dry with materialThe organic phase was dried with Na2SO4
5. filtrationfiltered
6. customevaporated
7. customto provide a beige powder