Citric Acid → HCID 9913922, compound

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Reaction Steps

In anhydrous methylene chloride (4 ml) are dissolved (2S)-2-[3-[(2RS)-2-carboxy-3-(phenylthio)propyl]-3-isoamylureido]-N-methyl-3-phenylpropionamide (Compound No. 36-2, 100 mg), 1-hydroxybenzotriazole (68 mg) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (96 mg) under a nitrogen atmosphere. Then, N-methylmorpholine (0.05 ml) is added to the solution under ice cooling, and the mixture is stirred for 30 minutes. Next, to the mixture is added a solution containing hydroxylammonium chloride (52 mg) and N-methylmorpholine (0.08 ml) in dimethylformamide (1 ml), and the mixture is stirred under ice cooling for 10 minutes and then at room temperature overnight. A 5% aqueous citric acid solution is added to the reaction mixture, and the whole is extracted with ethyl acetate. The organic layer is washed with a 5% aqueous sodium hydrogencarbonate solution and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 57 mg (54%) of the titled compound (Compound No. 40-1) as noncrystalline powder.

Provenance & Evidence