Hydrochloric Acid → (3R,4S,5S)-3-Amino-5-(3,5-difluoro-4-nitro-benzyl)-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol hydrochloride

Participants

Reaction Conditions

Reaction Steps

To [(3R,4S,5S)-5-(3,5-difluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester (0.873 g, 2 mmol) was added 4N HCl in dioxane (5 mL) and the reaction mixture was stirred for 3 h at 40° C. After evaporation the residue was stirred with Et2O, filtered and dried to provide the title compound as a beige solid: TLC (CH2Cl2-MeOH-AcOH-H2O 180:20:2:1) Rf=0.13; HPLC RtA=1.22 min; ESIMS [M+H]+=337; 1H NMR (600 MHz, DMSO-d6): δ 8.34 (s, 3H), 7.37 (d, 2H), 6.14 (d, 1H), 3.3-3.5 (m, 4H), 3.31 (d, 1H), 3.22 (d, 1H), 3.12 (m, 1H), 2.74 (dd, 1H), 2.26 (m, 1H).

Provenance & Evidence