Citric Acid → (3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(2H-tetrazol-5-yl)-amine

Participants

Reaction Conditions

Reaction Steps

(3,5-Bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-cyanamide (1.8 g) is dissolved in N,N-dimethylformamide (10 ml), and thereto are added sodium azide (407 mg) and ammonium chloride (335 mg), and the mixture is heated to 100° C. and stirred for 6 hours. The reaction solution is allowed to cool to room temperature, and thereto is added a 10% aqueous citric acid solution and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=30:1) to give (3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(2H-tetrazol-5-yl)-amine (1.9 g). MS (m/z): 618 [M+H]+

Provenance & Evidence