Lithium Hydroxide → 4-(1-{[2-Oxo-1-(4-trifluoromethylbenzyl)-2,3-dihydro-1H-indole-7-carbonyl]-amino}-cyclopropyl)-benzoic acid

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Reaction Steps

A mixture of 0.40 g of 2-oxo-1-(4-trifluoromethyl-benzyl)-2,3-dihydro-1H-indole-7-carboxylic acid, 0.29 g of (±)4-(1-amino-ethyl)-benzoic acid methyl ester, 0.19 g of HOBT-hydrate, 0.30 g of ethyl-dimethylaminopropyl-carbodiimide hydrochloride (EDC1) and 0.150 ml of N-methylmorpholine in 7 ml of DMF was stirred at room temperature for 16 h. The reaction was then quenched with 10 ml of water and 5 ml of sat. NaHCO3 solution. The resulting mixture extracted with 25 ml of EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to give the crude methyl ester (0.3 g) which was dissolved in 5 ml THF, 5 mL MeOH and treated with 4 mL of 1N LiOH solution. After stirring at 50° C. for 12 h, the reaction mixture was concentrated under reduced pressure to remove THF and MeOH. The residue was diluted with 8 mL of water and treated with 1 mL of AcOH with vigorous stirring. After stirring for 2 h, the solid was collected by filtration and air-dried to give 0.25 g of the title compound as a white powder.

Provenance & Evidence