Reaction Steps
A mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2-imidazolidinone(0.5 g) and chloromethyl pivalate (4.7 g) was stirred for 5 hours at 100° C. After having been cooled, the mixture was diluted with diisopropyl ether (10 ml), and the resulting powder was collected by filtration. The resulting powder was subjected to CHP-20P column chromatography (eluent: water→5% aqueous solution of acetonitrile→30% aqueous solution of acetonitrile→5% aqueous solution of tetrahydrofuran→10% aqueous solution of tetrahydrofuran→20% aqueous solution of tetrahydrofuran) to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-[3-(2,2-dimethylpropanoyloxy)methyl-1(1H)-1,2,3-triazolio]phenyl]-1-imidazolidinyl]butyl]-4-[(2,2-dimethylpropanoyloxy)methyl]-1H-1,2,4-triazolium dichloride (Compound 8, 134 mg) as a white powder and Compound 1 (141 mg) as a white powder. Compound 8: 1H-NMR(d6-DSMO) δ: 0.97(3H,d,J=6.8 Hz), 1.13(9H,s), 1.21(9H,s), 3.63-3.66(1H,m), 3.98-4.15(3H,m), 4.62-4.78(1H,m), 4.88(1H,d,J=14 Hz), 5.23(1H,d,J=14 Hz), 6.17(2H,s), 6.64(2H,s), 6.88(1H,s), 6.90-7.00(1H,m), 7.21-7.36(2H,m), 7.98(2H,d,J=9.8 Hz), 8.05(2H,d,J=9.8 Hz), 9.10(1H,s), 9.34(1H,d,J=2.0 Hz), 9.68(1H,d,J=2.0 Hz), 10.64(1H,s).
