ClCCl.[NH2:4][C@H:5]([CH3:22])[C@:6]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])([OH:13])[CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>O>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[C@@:6]([OH:13])([CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[C@H:5]([NH:4][S:31]([CH3:30])(=[O:33])=[O:32])[CH3:22]
To dichloromethane (10 ml) was added (2R,3R)-3-amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (0.54 g). To the mixture was added, under ice-cooling, triethylamine (0.28 ml), to which was added dropwise methanesulfonyl chloride (0.15 ml), followed by stirring for 15 minutes at room temperatures. To the mixture was added water (20 ml), which was subjected to extraction with dichloromethane (30 ml). The extract was washed with water (20 ml) and dried (MgSO4). Then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel chromatography (2.9×30 cm, eluent: ethyl acetate/methanol =25/1). The object fraction was concentrated to give N-[(2R,3R)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1H-1,2, 4-triazol-1-yl)-2-butyl]methanesulfonamide (Compound 49, 0.52 g) as a colorless oily product. 1H-NMR(CDCl3) δ: 1.04(3H,d,J=6.6 Hz), 3.07(3H,s), 4.12-4.21(1H,m), 4.81(1H,d,J=14 Hz), 4.97(1H,d,J=14 Hz), 5.28(1H,d,J=10 Hz), 6.69-6.82(2H,m), 7.27-7.39(1H,m), 7.79(2H,s)
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