Hydrochloric Acid → [4-[2-(4-Azidobenzoylamino)ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid

Participants

Reaction Steps

1 M NaOH (0.5 mL, 0.5 mmol) was added to a solution of [4-[2-(4-Azido-benzoylamino)-ethylamino]-5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid ethyl ester (8 mg, 0.015 mmol) in THF (0.5 mL) at ambient temperature. The reaction was stirred for 1 h, then acidified with 1 N HCl to pH 3. The reaction mixture was concentrated by rotary evaporation, and the resulting solid was filtered, washed with water and dried to yield the titled product (4 mg, 53%) as a white solid. 1H NMR: (d6-DMSO) δ 10.22 (s, 1H), 8.63 (m, 1H), 8.56 (s, 1H), 7.82 (d, 2H), 7.60 (m, 2H), 7.13 (m, 3H), 3.89 (s, 2H), 3.62 (m, 2H), 3.34 (m, 2H); HPLC: Rt=4.13 min; MS (ESI): m/z 509.07 (M−H)−.

Provenance & Evidence