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 → HCID 90253445, compound

Participants

Reaction Steps

rel-N-{[(3S,4R,6S)-6-(Cyclopropylmethyl)-3-(2,4-difluorophenyl)-4-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]carbamothioyl}benzamide (C72) 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 white solid. Yield: 430 mg, 0.97 mmol, 39%. LCMS m/z 443 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.22 (br d, J=7.2 Hz, 2H), 7.50 (t, J=7.2 Hz, 1H), 7.37-7.45 (m, 3H), 6.85-6.94 (m, 2H), 4.13 (q, J=8.5 Hz, 1H), 3.77 (d, J=12.0 Hz, 1H), 3.67-3.73 (m, 1H), 3.10-3.17 (m, 1H), 3.00 (dd, J=12.8, 3.0, 1H), 2.64 (dd, J=12.8, 2.8 Hz, 1H), 1.93 (q, J=12.4 Hz, 1H), 1.67-1.77 (m, 2H), 0.84-0.90 (m, 1H), 0.72-0.82 (m, 1H), 0.41-0.48 (m, 2H), 0.04-0.12 (m, 2H).

Provenance & Evidence