Hydrochloric Acid → 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester

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Reaction Steps

To a solution of 4.46 g of 2-thienyl-acetic acid in 80 ml of dry DMF 1.94 g of HOAT, 6.56 g of EDC and 9 ml of DIPEA were added at 0° C. After 30 min 7.48 g of 3-Amino-4-((1R,2R)-2-methyl-cyclohexylamino)-benzoic acid methyl ester were added, followed by the addition of 9 ml of DIPEA and the reaction was stirred at rt for 16 h. The reaction was then poured into water, brought to pH3 by the addition of 2 M aqueous hydrochloric acid and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated to obtain 9.52 g (86%) of 4-((1R,2R)-2-Methyl-cyclohexylamino)-3-(2-thiophen-2-yl-acetylamino)-benzoic acid methyl ester, which was used without further purification.

Provenance & Evidence