Diisopropylethylamine → HCID 59875627, compound

Participants

Reaction Steps

(2E)-4-tert-Butoxycarbonylamino-4-methylpent-2-enoic acid (143 mg, 0.62 mmol) was dissolved in dichloromethane (4 ml). 1-Hydroxy-7-azabenzotriazole (85 mg, 0.62 mmol) and subsequently N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (119 mg, 0.62 mmol) were added. The solution was stirred for 15 min at room temp. 5-((1R)-1-(Methyl((2R)-2-methylamino-3-(2-naphthyl)propionyl)amino)-2-phenylethyl)-[1,3,4]oxadiazol-2-carboxylic acid amide (230 mg, 0.52 mmol) was added. The solution was stirred for 5 min and ethyldiisopropylamine (0.11 ml, 0.62 mmol) was given to the reaction mixture. It was stirred for 16 h at room temp., diluted with ethyl acetate (20 ml) and extracted with water (20 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2×10 ml). The combined organic layers were washed with a saturated solution of sodium hydrogencarbonate and dried over magnesium sulfate. The crude product was purified by flash-chromatography on silica (40 g) with dichloromethane/ethyl acetate 1:1 to give 126 mg of ((E)-3-(((1R)-1-(((1R)-1-(5-carbamoyl-[1,3,4]oxadiazol-2-yl)-2-phenylethyl)methylcarbamoyl)-2-(2-naphthyl)ethyl)methylcarbamoyl)-1,1-dimethylallyl)carbamic acid tert-butyl ester.

Provenance & Evidence