Phosphorus pentachloride → HCID 57695533, compound

Participants

Reaction Steps

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid phenethyl-amide (193 mg, 0.33 mmole) was dissolved in anhydrous dichloromethane (5 ml), then phosphorus pentachloride (104 mg, 0.5 mmol) was added and the resulting solution was stirred at r.t. for 3 hr. TMSN3 (0.3 ml, neat) was added and the resulting mixture was stirred at r.t. for 3 hr. After quenching the reaction with sodium bicarbonate solution, the mixture was extracted with dichloromethane (3×20 ml). The combined organic were dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 5-(4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-yl)-1-phenethyl-1H-tetrazole (201 mg, 89%). M.p.: 118-120° C.; 400 MHz 1H NMR (CDCl3, δ: 7.32-7.23 (m, 8H), 7.19-7.07 (m, 8H), 6.92 (s, 1H), 6.90 (s, 1H), 6.87 (d, J=8.0 Hz, 1H), 6.68 (s, 1H), 5.05 (s, 2H), 4.99 (s, 2H), 4.43 (t, J=7.6 Hz, 2H), 3.70 (s, 3H), 3.11 (t, J=7.6 Hz, 2H), 2.92-2.84 (m, 1H), 1.24 (d, J=7.2 Hz, 6H); LCMS: 611 [M+H].

Provenance & Evidence