Hydrochloric Acid → (2S,3S)-2-amino-4-hydroxy-N-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)butanamide hydrochloride

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Reaction Steps

tert-Butyl (2S,3S)-4-(tert-butyldimethylsilyloxy)-1-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-ylamino)-1-oxo-3-(4-trifluoromethylphenyl)butan-2-ylcarbamate (0.014 g, 0.020 mmol) was taken up in 2 mL of 4 N HCl in dioxane. After 1.5 hours, a white precipitate formed. The precipitate was collected by filtration to provide (2S,3S)-2-amino-4-hydroxy-N-(5-(isoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-3-(4-(trifluoromethyl)phenyl)butanamide hydrochloride (1.2 mg, 12%). LCMS (M+H) 474 calc. for C22H19F3N5O2S 474.1. 1H NMR (400 MHz, CD3OD): δ ppm 9.84-9.78 (m 1H), 8.90-8.55 (m, 6H), 7.80-6.58 (m, 3H), 4.83-4.72 (m 2H), 4.09-3.90 (m, 1H), 3.72-3.54 (m, 1H). 4H not detected.

Provenance & Evidence