Trifluoroacetic acid → Biphenyl-4-carboxylic acid (6-amino-2-hydroxyindan-1-yl)amide

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Reaction Steps

Combine (6-amino-2-hydroxyindan-1-yl)carbamic acid tert-butyl ester (1.5 g, 5.68 mmol) with 5 mL of TFA at 0° C. Stir the mixture for 1 h and then evaporate to dryness. Added 3.0 mL of triethylamine and 30 mL of methylene chloride the residue. To this mixture, add a solution of biphenyl-4-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester (1.76 g, 5.96 mmol) in 15 mL of methylene chloride. Stir the resulting mixture for 12 h. Evaporate solvent and purify the residue by a column chromatography (silica gel/MeOH:CH2Cl2=9:1) to give 1.88 g (96% yield) of biphenyl-4-carboxylic acid (6-amino-2-hydroxyindan-1-yl)amide; MS 345 (MH+).

Provenance & Evidence