Phosphorus pentachloride → HCID 57695530, compound

Participants

Reaction Steps

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid-(3-methoxypropyl)-amide (183 mg, 0.33 mmole) was dissolved in anhydrous dichloromethane (5 ml), then PCl5 (0.5 mmol) was added and the resulting solution was stirred at r.t. for 3 hr. TMSN3 (0.3 ml, neat, excess) was added and the resulting mixture was stirred at r.t. for 3 hr. After quenching the reaction with NaHCO3 solution, and extracting with dichloromethane (20 ml×3), the combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give product 5-(4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-yl)-1-(3-methoxy-propyl)-1H-tetrazole (166 mg, 87%). M.p.: 102-104° C.; 400 MHz 1H NMR (CDCl3) δ: 7.43 (s, 1H), 7.35-7.13 (m, 12H), 6.87 (d, J=8.0 Hz, 1H), 6.70 (s, 1H), 5.07 (s, 2H), 5.03 (s, 2H), 4.34 (t, J=7.2 Hz, 2H), 3.72 (s, 3H), 3.24 (t, J=6.0 Hz, 2H), 3.16 (s, 3H), 2.93-2.81 (m, 1H), 2.06 (pent, J=6.4 Hz, 2H), 1.23 (d, J=6.9 Hz, 6H); LCMS: 579 [M+H].

Provenance & Evidence