Dimethylformamide → tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy) (2-[(methoxycarbonyl)amino]benzimidazol-5-ylsulfonyl)amino-2-hydroxypropyl)carbamate

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Reaction Steps

tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate (step 1, Example 54), (0.75 g, 2.1 mmol) was combined with 2-(methoxycarbonyl)amino benzimidazol-5-ylsulfonyl chloride (0.89 g, 3.1 mmol) in anhydrous DMF (15 ml) under a N2 atmosphere. Diisopropylethylethyl amine (1.08 ml, 6.2 mmol) was added and the reaction was stirred at room temperature for 24 hours. The 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 flash chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% to 3% to 4%). Recovered 0.79 g (62%) of product as a white foam. Rf=0.08 (3% MeOH/CH2Cl2). HPLC tR=10.47 min (C18 column). LRMS (M+H)+ 618.2.

Provenance & Evidence