Ammonia → HCID 53670432, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(tert-Butoxycarbonylamino-methyl)-2-hydroxy-benzoic acid (20.0 g, 74.9 mmol) in 700 mL tetrahydrofuran at 0° C. was added 4-methyl morpholine (12.3 mL, 112.3 mmol), 1-hydroxybenzo-triazole (15.2 g, 112.3 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (21.5 g, 112.3 mmol). Stir for 1 hour at 0° C., then added concentrated ammonium hydroxide (15.2 mL, 112.3 mmol). The reaction was allowed to warm slowly to room temperature and stirred overnight. The reaction was then diluted with ethyl acetate and washed with 5% citric acid (3×250 mL), saturated sodium bicarbonate (3×250 mL), and saturated sodium chloride (1×250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a pale yellow powder. The powder was collected and washed with ether, followed by drying under reduced pressure to yield (14.0 g, 71%). 1H NMR (400 MHz, DMSO): δ 12.77 (bs, 1H), 8.33 (bs, 1H), 7.72 (d, 1H), 7.28 (d, 2H), 6.84 (d, 1H), 4.05 (d, 2H), 1.38 (s, 9H); Mass Spectrum (Chemical Ionization, 1% NH3 in CH4) m/z 267 (M+H).

Provenance & Evidence