N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide → rel-N-[(4aR,6R,8aS)-6-cyclopropyl-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide

Participants

Reaction Steps

rel-N-{[(3S,4R,6R)-6-Cyclopropyl-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C21) was converted to the product using the method described for synthesis of N-[(4aR,6R,8aS)-6-[(benzyloxy)methyl]-8a-(2,4-difluorophenyl)-4,4a,5,6,8,8a-hexahydropyrano[3,4-d][1,3]thiazin-2-yl]benzamide (C8) in Preparation P1. The product was obtained as a solid. Yield: 1.42 g, 3.31 mmol, 88%. LCMS m/z 429.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 11.7-12.5 (v br s, 1H), 8.24 (br d, J=7.6 Hz, 2H), 7.48-7.54 (m, 1H), 7.38-7.48 (m, 3H), 6.82-6.97 (m, 2H), 4.08 (br dd, J=12.4, 1.3 Hz, 1H), 3.80 (d, J=12.3 Hz, 1H), 3.05-3.13 (m, 1H), 2.93-3.04 (m, 2H), 2.64 (dd, J=12.8, 2.6 Hz, 1H), 2.05-2.18 (m, 1H), 1.75-1.83 (m, 1H), 0.96-1.06 (m, 1H), 0.50-0.62 (m, 2H), 0.40-0.46 (m, 1H), 0.22-0.29 (m, 1H).

Provenance & Evidence