Hydrochloric Acid → N-((4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-(hydroxymethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

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Reaction Steps

N-((4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-((trityloxy)methyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide, obtained in preparation example 1-(5), (8.42 g) was suspended in methanol (100 mL) and water (3 mL) and conc. hydrochloric acid (5 mL) were added. The reaction mixture was stirred vigorously overnight, and then concentrated under reduced pressure to a volume of about 30 mL. The mixture was then carefully neutralised with NaHCO3 (sat., aq., 100 mL) and extracted with EtOAc (3×100 mL). The combined organic portions were dried over MgSO4, evaporated, and the residue purified by silica gel column chromatography (0% to 50% EtOAc in hexanes) to afford the title compound (4.20 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.94 (br. s., 1H), 2.83 (d, J=10.6 Hz, 1H), 3.14-3.49 (m, 2H), 3.77 (d, J=8.8 Hz, 1H), 3.97 (dd, J=11.7, 2.7 Hz, 1H), 4.08 (d, J=6.3 Hz, 1H), 4.46-4.63 (m, 2H), 7.07-7.25 (m, 3H), 7.37-7.60 (m, 3H), 8.00-8.26 (m, 2H)

Provenance & Evidence