反应详情

(1-Benzyl-3-{[3-(1-cyclopentyl-pyrrolidin-3-ylamino)-4-nitro-benzenesulfonyl]-isobutyl-amino}-2-hydroxy-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester (12) (0.36 g, 0.50 mmol, 1 equiv), ammonium formiate (0.16 g, 2.50 mmol, 5 equiv) and palladium on charcoal (10%, 0.106 g, 1.00 mmol, 2 equiv) were suspended in 2-methyl-tetrahydro-furan. The solution was heated to reflux for 2 h. The catalyst was filtered over a bed of dicalite and the filtrate was evaporated under reduced pressure. The crude product was purified by column chromatography on elution with dichloro-methane:ammonia in methanol (7N) (99:1 to 97.5:2.5). The solvent was evaporated under reduced pressure. (0.10, 0.50 mmol, 29%). LRMS (ES+): m/z 700 [M+H]+; HPLC (system 1) (272 nm) tR 6.95 min, 94%; 1H-NMR (CDCl3) δ 0.89 (d, 3H, CH3), 0.92 (d, 3H, CH3), 1.39-2.10 (m, 17H, CH2, H4, CH and CH2 (7x)), 2.70-3.21 (m, 9H, CH2—N, CH2—N (isobutyl), CH, H3a, CH—NH and CH—N), 3.59-3.78 (m, 3H, CH, H5, CH, H2 and CH), 3.78-3.99 (m, 3H, CH, H2, CH, H5 and CH—OH), 4.32-4.43 (brs, 1H, NH), 4.60-4.76 (brs, 1H, NH), 4.90-5.08 (m, 1H, CH, H3), 5.62 (d, 1H, CH, H6a), 6.62 (d, 1H, CHarom), 6.87 (s, 1H, CHarom), 7.07 (dd, 1H, CHarom), 7.18 (d, 1H, OH), 7.22-7.31 (m, 5H, C6H5).

1. temperatureThe solution was heated
2. temperatureto reflux for 2 h
3. filtrationThe catalyst was filtered over a bed of dicalite
4. customthe filtrate was evaporated under reduced pressure
5. customThe crude product was purified by column chromatography on elution with dichloro-methane
6. customThe solvent was evaporated under reduced pressure