Tetrahydrofuran → 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-phenoxycarbonylaminophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 3-[5-(4-aminophenyl)-1-(4-carbamoyl-2-methylphenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (11A, synthesis described in Scheme 4 where R1=4-carbamoyl-2-methylphenyl) (106 mg, 0.26 mmol) was dissolved in 1 mL methylene chloride. The mixture was cooled in an ice bath. Hünig's base (0.12 mL, 0.65 mmol) was added. Phenylcarbamate (0.05 mL, 0.39 mmol) was added dropwise. The reaction was stirred at 0° C. for 30 min, and then allowed to warm to room temperature. After 24 hrs, 3 mL THF/3 mL sodium bicarbonate was added and stirred for 40 min. Then ethyl acetate (3 mL) was added and the layers separated. The aqueous layer was further extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by preparative TLC plate (1500 microns, 5% MeOH/CH2Cl2). The desired band (rf=0.51) was isolated and dried under high vacuum to yield 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-phenoxycarbonylaminophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (13B) (66 mg, 48%, hygroscopic tan powder).

Provenance & Evidence