Triethylamine → HCID 53973617, compound

Participants

Reaction Conditions

Reaction Steps

5-((1R)-1-Methylamino-2-phenylethyl)-[1,3,4]oxadiazole-2-carboxylic acid amide (240 mg, 0.98 mmol), (R)-2-((tert-butoxycarbonyl)methylamino)-3-(2-naphthyl)propionic acid (320 mg, 0.98 mmol) and 1-hydroxy-7-azabenzotriazole (133 mg, 0.98 mmol) were dissolved in dichloromethane (8 ml) and DMF (4 ml). The solution was cooled to 0° C. and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (230 mg, 1.18 mmol) was added. After 10 min triethylamine (0.35 ml, 2.46 mmol) was added. The solution was stirred for 1 h at 0° C. and subsequently for 16 h at room temp. The solution was diluted with ethyl acetate (30 ml) and water (20 ml). The phases were separated and the aqueous phase was extracted with ethyl acetate (20 ml). The combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (30 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g) with ethyl acetate to give 301 mg of ((1R)-1-(((1R)-1-(5-carbamoyl-[1,3,4]oxadiazol-2-yl)-2-phenylethyl)methylcarbamoyl)-2-(2-naphthyl)ethyl)methylcarbamic acid tert-butylester.

Provenance & Evidence