Sodium ethoxide → N-{3-[(4aR,7aS)-1-(4-fluorobenzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-cyclopenta[b]pyridin-3-yl]-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-2-{(4-fluoro-benzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclopentanecarboxylic acid ethyl ester (0.044 g, 0.076 mmol) in ethanol (10 mL) was added a 21% w/w solution of sodium ethoxide in ethanol (0.0981 g, 0.303 mmol) and the reaction mixture was heated at 60° C. for 16 h. Upon cooling the reaction mixture was quenched with a 1.0 M aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the solvent was removed in vacuo to afford the crude product, which was further purified by prep-HPLC to afford cis-N-{3-[1-(4-fluoro-benzyl)-4-hydroxy-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (0.0241 g, 0.045 mmol, 59.4%), as a solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.48-1.55 (4H, m), 1.95-2.10 (4H, m), 3.07 (3H, s), 3.34 (1H, bs), 3.86 (1H, bs), 4.48 (1H, d, J=14.7 Hz), 4.91 (1H, d, J=14.8 Hz), 7.16 (2H, t, J=8.9 Hz), 7.40 (2H, t, J=6.6 Hz), 7.52 (1H, d, J=10.7 Hz), 7.59 (2H, d, J=8.4 Hz), 10.18 (1H, s). LC-MS (ESI) calcd for C23H23FN4O6S2 534.10, found 535.4 [M+H+].

Provenance & Evidence