Citric Acid → HCID 51034413, compound

Participants

Reaction Steps

130 mg (0.4 mmol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate and 0.2 ml (1.2 mmol) of diisopropylethylamine are added to a solution of 185 mg (0.4 mmol) of (S)-3-[4-(2-bromopyridin-4-ylmethoxy)benzoylamino]-2-piperidin-1-ylpropanoic acid in 10 ml of dimethylformamide. After stirring for 20 minutes at ambient temperature, 65 mg (0.4 mmol) of O-tert-butyldimethysilylhydroxylamine diluted in 3 ml of dimethylformamide are added. The reaction medium is stirred at ambient temperature for 18 h, then hydrolysed with 1 ml of an aqueous solution of 5% citric acid and 2 ml of water. After stirring at ambient temperature for 1 h, the mixture is brought to pH=8 with a saturated aqueous solution of sodium hydrogen carbonate then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under vacuum. The crude product obtained is precipitated in an 8/2 heptane/ethyl acetate mixture then filtered. The residue obtained is recrystallized in ethyl acetate. 20 mg (10%) of 4-(2-bromopyridin-4-ylmethoxy)-N—((S)-2-hydroxycarbamoyl-2-piperidin-1-ylethyl)benzamide are obtained in the form of a pale-yellow solid having a melting point of 150° C.

Provenance & Evidence