Cesium carbonate → HCID 59997340, compound

Participants

Reaction Steps

A mixture of 59 mg (0.1 mMol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate, 120 mg of 2-chloro-5-cyanopyridine and 65 mg (0.2 mMol) of cesium carbonate in 0.5 mL of dimethyl formamide was stirred at rt for 5 h. The mixture was diluted with ethyl acetate and extracted with water. Evaporation of the solvent and chromatography on silica gel (1:1 ethyl acetate-hexanes) gave the title compound (16 mg). 1H NMR: 0.88(6H,dd), 1.55-1.8(3H,m), 2.8-3.2(7h,m), 3.65(2H,m), 3.8(2H,m), 3.95(1H,m), 5.0(2H,m), 5.6(1H,d), 6.05(2H,s), 6.82(1H,d), 6.95(1H,d), 7.0(2H,d), 7.1-7.4(4H,m), 7.9(1H,d), 8.4(1H,bs). MS: 695(M+H)

Provenance & Evidence