Trimethylsilyl iodide → HCID 68827544, compound

Participants

Reaction Steps

TMS-I (870 mg, 0.63 mL, 4.35 mmol) was added dropwise to a stirred solution of (2R)-methyl-2-tert-butoxycarbonylamino-3-(4′-dibenzofuran-4-yl-biphenyl-4-ylmethyl-sulfanyl)-propionate (2.24 g, 3.96 mmol) in anhydrous methylene chloride (50 mL). The reaction mixture was stirred at room temperature for 20-30 mins (TLC control), and then diluted with water (50 mL). Saturated sodium bicarbonate solution was added to adjust the solution to pH 8-9. The reaction mixture was extracted with diethyl ether (2×50 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 5% methanol in methylene chloride as eluent, afforded the title compound has a pale yellow solid (1.76 g, 95%); Rf: 0.20 (5% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz): δ 8.00 (3H, d, J=8 Hz, Ar—H), 7.94 (1H, d, J=8 Hz, Ar—H), 7.76 (2H, d, J=9 Hz, Ar—H), 7.64 (4H, m, Ar—H), 7.34-7.51 (5H, m, Ar—H), 3.81 (2H, s, PhCH2S), 3.75 (3H, s, OMe), 3.67 (1H, m CHN), 2.91 (1H, dd, J=15, 5 Hz, CHHCHN), 2.86 (1H, dd, J=15, 8 Hz, CHHCHN), 1.91 (2H, s, NH2); ESI-LCMS e/z calcd for C29H25NO3S 467.586, found 468 (M+H)+.

Provenance & Evidence