Pyrrole → 1-Methyl-4-[1-methyl-4-[2-[4-(trifluoromethyl)phenylsulfonyl]ethoxycarbonylamino]-2-imidazolylcarbonylamino]-1H-pyrrole-2-carboxylic acid methyl ester

Participants

Reaction Steps

1-Methyl-4-nitropyrrole-2-carboxylic acid methyl ester (65.68 mg, 0.3567 mmol) was dissolved in EA (10 ml) and 10% Pd/C (10 mg) was added thereto. The reaction solution was stirred for 10 hours at room temperature under hydrogen atmosphere to reduce a nitro group (NO2) into an amino group (NH2), whereby a pyrrole-type amino acid was obtained. 10% Pd/C was filtered out by celite 545 and the filtrate was washed with EA and methanol. 1-Methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl)-ethoxycarbonylamino]-1H-imidazole-2-carboxylic acid (50.10 mg, 0.1187 mmol) dissolved in a solvent mixture of anhydrous) MF (6 ml) and DCM (2 ml) was added thereto, TFFH (83.37 mg, 0.3567 mmol), HOBt (64.73 mg, 0.4748 mmol) and DIEA (82.84 ml, 0.4748 mmol) were also added thereto, and the reaction solution was reacted according to the same procedure as Step (4-1) of Example 2 to give 1-methyl-4-({1-methyl-4-[2-(4-trifluoromethyl-benzenesulfonyl)ethoxycarbonylamino]-1H-imidazole-2-carbonyl}-amino)-1H-pyrrole-2-carboxylic acid methyl ester (41.7 mg, 63.01%) of a pale yellow solid.

Provenance & Evidence