Sodium hydride → HCID 86701097, compound

Participants

Reaction Steps

To a solution of tert-butyl (3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(propyl)carbamate (20 g, 42 mmol) in DMF (300 mL) was added sodium hydride (10 g, 417 mmol) at 15° C. in portions, followed by addition of 1-(bromomethyl)-4-methoxybenzene (33.8 g, 168 mmol). The resulting solution was stirred for 1.5 h at room temperature, quenched by addition of cold water (100 mL), and extracted with dichloromethane (5×100 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum to provide a residue, which was purified by silica gel column, eluted with 10-25% ethyl acetate in petroleum ether to give compound 18 as a yellow oil (20 g, 64.8%). (ES, m/z): 717.1; 1H NMR (300 MHz, CDCl3) δ 7.32-7.35 (d, J=8.7 Hz, 2H), 7.19-7.22 (d, J=8.7 Hz, 2H), 6.83-6.92 (m. 4H), 6.05-6.07 (d, J=6.9 Hz, 1H), 4.57-4.74 (m, 3H), 4.30-4.39 (m, 2H), 4.14-4.17 (t, J=4.2 Hz, 1H), 3.68-3.84 (m, 11H), 3.41-3.45 (m, 1H), 1.67-1.74 (m, 2H), 1.53 (s, 9H), 0.89 (s, 9H), 0.84 (m, 3H), 0.08 (s, 6H).

Provenance & Evidence