Hydrochloric Acid → HCID 135955883, compound

Participants

Reaction Conditions

Reaction Steps

cis-2-{(4-Fluoro-benzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclooctanecarboxylic acid methyl ester (0.241 g, 0.396 mmol) was dissolved in ethanol (4 mL), a 21% w/w solution of sodium ethoxide in ethanol (0.739 mL, 1.98 mmol) was added. The mixture was stirred at 60° C. for 4 h and allowed to cool to 25° C. The mixture was poured into a 0.5 M aqueous hydrochloric acid solution (100 mL). The product started to precipitate and was collected by vacuum filtration. The precipitate was washed with water and dried under high vacuum to afford the pure product N-{3-[1-(4-fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (0.07 g, 0.121 mmol, 31%), as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.24-1.83 (12H, m), 3.04 (3H, s), 3.73-3.58 (2H, m), 4.21-4.46 (1H, m),4.99 (1H, d, J=16 Hz), 7.18 (2H, t, J=8 Hz), 7.47-7.53 (6H, m), 10.08 (1H, s). LC-MS (ESI) calcd for C26H29FN4O6S2 576.15, found 577.5 [M+H+].

Provenance & Evidence