Sodium hydride → HCID 69085628, compound

Participants

Reaction Steps

To a solution of (3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol (1 g, 2.76 mmol) in DMF (20 mL) was added sodium hydride (568 mg, 16.6 mmol, 70%) at 15° C., and followed by addition of 1-(bromomethyl)-4-methoxybenzene (2.22 g, 11.0 mmol). The resulting solution was stirred for 3 h at room temperature, quenched by addition of cold water (50 mL), and extracted with dichloromethane (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by silica gel column, eluted with 10-25% ethyl acetate in petroleum ether to give compound 9 as a yellow oil (1.2 g, 64%). (ES, m/z): [M+H]+ 603.1; 1H NMR (300 MHz, CDCl3) δ 7.22-7.35 (m, 4H), 6.84-6.92 (m, 4H), 6.27-6.29 (d, J=6.6 Hz, 1H), 4.60-4.76 (m, 4H), 4.36-4.43 (m, 2H), 4.10-4.17 (m, 2H), 3.81 (s, 6H), 3.72 (m, 1H), 3.61 (m, 1H), 2.99 (s, 6H), 0.83 (s, 9H), 0.07 (s, 6H).

Provenance & Evidence