Diisopropylethylamine → HCID 178454607, compound

Participants

Reaction Steps

To 80 mg (0.24 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propanoic acid (cf. preparation 2-3) dissolved in 2.75 mL of dichloromethane and 1.25 mL of dimethylformamide are added 0.08 mL (0.48 mmol) of diisopropylethylamine, 84 mg (0.26 mmol) of TBTU and 88 mg (0.26 mmol) of 3-phenylazetidin-3-yl butyrate trifluoroacetate. After 2 hours, the solution is washed with 1N sodium hydroxide solution and the organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product obtained is chromatographed by preparative TLC (eluent: 9/1 dichloromethane/methanol). 5.4 mg of 1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]-ureido}-3-(4-methoxyphenyl)propionyl]-3-phenylazetidin-3-yl butyrate are obtained in a yield of 2%.

Provenance & Evidence