反应详情

温度

0 °C

(3S,3aR,6aS) Hexahydrofuro[2,3-b]furan-3-yl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate (0.050 g, 0.1 mmol) was combined with 2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chloride (0.055 g, 0.2 mmol) in anhydrous DMF (1 ml) under a N2 atmosphere. The resulting solution was chilled to 0° C. and diisopropylethylethyl amine (0.062 ml, 0.4 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 24 hours. Reaction mixture was diluted in EtOAc and washed with sat. NaHCO3, 0.5N KHSO4 and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purification by preparative TLC (5% MeOH/EtOAc). Recovered 0.051 g (62%) of the product as a white foam. Rf=0.42 (5% MeOH/EtOAc). 1H NMR (CDCl3) 8.09 (1H,s), 7.76 (1H,d), 7.39 (1H,d), 7.32-7.12 (5H,m), 6.54-6.40 (2H,m), 5.67 (1H,d), 5.10-4.92 (2H,m), 4.85 (1H,m), 4.00-3.83 (3H,m), 3.82-3.70 (2H,m), 3.62-3.51 (1H,m), 3.38 (1H,m), 3.31 (3H,s), 3.10 (1H,m), 3.04-2.80 (4H,m), 1.92-1.70 (6H,m), 1.69-1.44 (4H,m). LRMS (M+H)+ 694.1.

1. temperatureto warm to room temperature
2. customReaction mixture
3. washwashed with sat. NaHCO3, 0.5N KHSO4 and brine
4. dry with materialOrganic phase was dried with MgSO4 and solvent
5. customwas removed in vacuo
6. customPurification by preparative TLC (5% MeOH/EtOAc)
7. customRecovered 0.051 g (62%) of the product as a white foam