Benzyl Bromide → HCID 86701109, compound

Participants

Reaction Steps

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(2-fluoroethyl)carbamate (2.0 g, 4.2 mmol) in N,N-dimethylformamide (30 mL) was treated with sodium hydride (510 mg, 21 mmol) for 10 min at 10° C. in a nitrogen atmosphere, and followed by addition of 1-(bromomethyl)benzene (2.2 g, 13 mmol). After stirred for 15 min, the reaction was quenched with saturated aqueous NH4Cl and extracted with dichloromethane (3×30 mL). The organic layers were dried over anhydrous magnesium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 1.5-3% ethyl acetate in petroleum ether to provide compound 70 as a yellow oil (0.7 g, 25%). (ES, m/z) [M+H]+ 660.8; 1H NMR (300 MHz, CDCl3) δ 7.28-7.43 (m, 10H), 6.11-6.13 (d, J=6.3 Hz, 1H), 4.60-4.74 (m, 4H), 4.30-4.41 (m, 6H), 3.73-3.75 (m, 3H), 3.37-3.44 (m, 1H), 1.54 (s, 9H), 0.90 (s, 9H), 0.06 (s, 6H).

Provenance & Evidence