反应详情

To a solution of benzyl (N-{3-[(1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-7-ylmethyl}amino)sulfonylcarbamate (120 mg, 0.17 mmol) in methanol (20 mL) was added 10% palladium on carbon (60 mg). The mixture was degassed and stirred under an atmosphere of hydrogen gas (balloon) overnight. The resulting mixture was filtered through a pad of Celite. The organic was concentrated in vacuo. The residue was purified via flash column chromatography (Teledyne Isco RediSep column; 0-3% methanol in dichloromethane) to afford the desired product, N-{3-[(1R,2S,7R,8S)-3-(4-fluoro-benzyl)-6-hydroxy-4-oxo-3-aza-tricyclo[6.2.1.02,7]undec-5-en-5-yl]-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-7-ylmethyl}-sulfamide (89 mg, 0.15 mmol, 88%), as a white solid. 1H NMR (400 MHz, CDCl3) δ: 1.19-1.79 (6H, m), 2.57-2.58 (1H, m), 2.83-2.88 (2H, m), 3.49 (1H, d, J=9.6 Hz), 4.22 (1H, d, J=15.6 Hz), 4.48 (2H, d, J=6.4 Hz), 4.55 (2H, bs), 5.16 (1H, d, J=14.8 Hz), 5.29-5.32 (1H, m), 7.03-7.07 (3H, m), 7.19-7.22 (2H, m). LC-MS (ESI) calculated for C23H24FN5O6S3 581.66. found 582.2 [M+H+].

1. customThe mixture was degassed
2. filtrationThe resulting mixture was filtered through a pad of Celite
3. concentrationThe organic was concentrated in vacuo
4. customThe residue was purified via flash column chromatography (Teledyne Isco RediSep column; 0-3% methanol in dichloromethane)