triethylamine; mercury dichloride; sodium acetate; sodium hydroxide; n,n-dimethyl-formamide; methanol; methanol; water;
reactants are commercially availlable.
blagg, julian, wo2011/35009, a1, (2011) preparation of intermediate ddto a mixture of intermediate cc (200 mg, 1.049 mmol), et3n (0.436 ml, 3.14 mmol), and l ,3-dicarbomethoxy-2-methyl-2-thiopseudourea (216 mg, 1.049 mmol) in dmf (8 ml) was added hgcl2 (284 mg, 1.049 mmol) at room temperature (26 °c). the mixture was stirred overnight. th e reaction mixture was then filtered, and the filtrate was diluted with h20 (50 ml), extracted with etoac (-150 ml), washed with h20 (50 ml) and brine solution (50 ml), dried (na2sc>4), filtered, and evaporated to obtain crude intermediate dd (150 mg). this material was used in the next step without any further characterization and purification. rf = 0.3 (20percenteto ac/petroleum ether). mass: (m z=313.1).preparation of compound (33)to a solution of intermediate dd (150 mg, 0.48 mmol) in meoh ( 10 ml) was added naome (129 mg, 2.40 mmol) at 0 °c. the reaction was warmed to room temperature and stirred overnight. the reaction mixture was concentrated, and in aqueous naoh (2.5 ml) was added. t he reaction was heated to 60 °c for 30 minutes. the reaction mixture was evaporated to obtain a crud e residue that was purified by column chromatography (100-200 mesh silica gel, 20percent) meoh/chcl3 /aq. nh3) to obtain compound (33) (15 mg, 9.6percent). rf = 0.6 (20percent meoh/chcl3/0.1 ml aqueous nh3). 1h-nmr (400mhz, dmso-j6) delta 11.36 and 1 1.20 (2 overlapped br. s, exchanged with d20, 2h), 7.05 (s, 1h), 6.05 (br. s, exchanged with d20, 2h), 5.88 (d, j = 2.4hz, 1h). mass (m/z): 150.7 (m l). lcms: (column: zodiacsil 120-5-c- 18-aq (4.6 chi 50 mm), mobile phase: a: 0.01m hcoonh4 (aq); b: meoh, t/percentb: 0/5, 10/90, 10.1/5, flow: 1.0 ml/min, diluent: meoh), rt=2.379 min, 97.08 (214 nm), 98.26 (254 nm).
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