Hydrochloric Acid → 2-Amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester hydrochloric acid salt

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2-Amino-3-methylbutyric acid 2-{[6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carbonyl]-aminooxy}-ethylester (325 mg) was dissolved in about 1.5 mL of absolute EtOH, and 0.35 mL of 2N HCl in ether was added to give a thick precipitate. As additional 1.5 mL of ether were added to make the slurry thin. The slurry was mixed for 5-10 minutes and concentrated on a rotary evaporator. The damp solids were slightly yellowish and dried under high vacuum at room temperature overnight to give 0.325 g (94%) of the HCl salt. 1H NMR (400 MHz, DMSO-d6) δ: 0.97 (d, J=6.6 Hz, 3H), 1.00 (d, J=6.6 Hz, 3H), 2.20 (m br, 1H), 3.91 (s, 3H), 3.95 (s br, 1H), 4.09 (m br, 2H), 4.34 (m br, 1H), 4.43 (m br, 1H), 6.37 (dd, JH-H=8.8 Hz, JF-H=4.3 Hz virtual coupling, 1H), 7.27 (dd, J=8.8 Hz, 2.3 Hz, 1H), 7.65 (d, J=2.2 Hz, 1H), 7.78 (s, 1H), 7.92 (s, 1H), 8.37 (s br, 3H), 8.43 (s, 1H), 11.86 (s br, 1H). 19F NMR (376 MHz, DMSO-d6) δ: −132.98.

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