Dimethylformamide → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-{4-[(3-cyanobenzyl)oxy]benzyl}-3-[(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate

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49 mg of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(2,3-dihydro-1,4-benzodioxin-6-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxy benzyl)propylcarbamate, 20 mg of m-cyanobenzylchloride, 20 mg of cesium carbonate and 0.5 mL of dimethyl formamide were stirred at rt for 5 h. The mixture was diluted with ethyl acetate and extracted with water. Chromatography on silica gel (1:1 ethylacetate/hexane) gave the title compound as a white solid (26 mg). 1H NMR: 0.87(6H,dd), 1.58(2H,m), 1.8(1H,m), 2.75(2H,m), 2.9(4H,m), 3.1(1H,m), 3.62(3H,m), 3.8(3H,m), 3.95(1H,m), 4.25(4H,m), 4.95(2H,m), 5.0(2H,s), 5.62(1H,d), 6.82(2H,d), 6.92(1H,d), 7.1(2H,d), 7.2(2H,m), 7.45(1H,t), 7.6(2H,m), 7.75(1H,s). MS:722 (M+H)

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