1-Hydroxybenzotriazole → Ethyl 4-({2-[(3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyrate

Participants

Reaction Steps

2-[(3,5-Bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carboxylic acid (200 mg) is dissolved in N,N-dimethylformamide (5 ml) and thereto are added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (86 mg), 1-hydroxy-benzotriazole (60 mg), triethylamine (125 μl) and 4-aminobutyric acid ethyl ester hydrochloride (75 mg), and the mixture is stirred at room temperature overnight. To reaction mixture is added a saturated aqueous sodium bicarbonate 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 (hexane:ethyl acetate=5:2) to give ethyl 4-({2-[(3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyrate (230 mg). MS (m/z): 785 [M+H]+

Provenance & Evidence