Reaction SMILES: [F:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:21][C:22]2[CH:23]=[C:24]([C:32]3[C:37]([CH3:38])=[CH:36][C:35]([O:39][CH:40]4[CH2:45][CH2:44][S:43](=[O:46])[CH2:42][CH2:41]4)=[CH:34][C:33]=3[CH3:47])[C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51].ClC1C=CC=C(C(OO)=[O:63])C=1>C(OCC)(=O)C>[O:46]=[S:43]1(=[O:63])[CH2:44][CH2:45][CH:40]([O:39][C:35]2[CH:34]=[C:33]([CH3:47])[C:32]([C:24]3[C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=[C:22]([CH2:21][N:8]([S:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N+:18]([O-:20])=[O:19])(=[O:10])=[O:11])[C:6]4[CH:5]=[CH:4][C:3]([CH2:48][CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[C:2]([F:1])[CH:7]=4)[CH:23]=3)=[C:37]([CH3:38])[CH:36]=2)[CH2:41][CH2:42]1
Reactant: CCOC(=O)CCc1ccc(N(Cc2ccc(OC(C)C)c(-c3c(C)cc(OC4CCS(=O)CC4)cc3C)c2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1F
Reactant: O=C(OO)c1cccc(Cl)c1
Solvent: CCOC(C)=O
Product: CCOC(=O)CCc1ccc(N(Cc2ccc(OC(C)C)c(-c3c(C)cc(OC4CCS(=O)(=O)CC4)cc3C)c2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1F
Temperature: 0 °C
Yield: 93 %

Procedure:
To a solution of ethyl 3-(2-fluoro-4-{[(4′-hydroxy-6-isopropoxy-2′,6′-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (0.59 g, 0.89 mmol), tetrahydro-2H-thiopyran-4-ol (0.12 g, 0.98 mmol) and triphenylphosphine (0.30 g, 1.16 mmol) in tetrahydrofuran (8 mL) was added diethyl azodicarboxylate (40% toluene solution, 0.53 mL, 1.16 mmol) under stirring at room temperature, and the mixture was stirred for 1 hr. To the reaction mixture were added reagents (tetrahydro-2H-thiopyran-4-ol, triphenylphosphine and diethyl azodicarboxylate) in the same amount as mentioned above, and the mixture was further stirred for 24 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=2/1) to give an oil (0.64 g). To a solution of the obtained oil in ethyl acetate (9 mL) was added m-chloroperbenzoic acid (70%, 0.44 g, 1.78 mmol) under stirring at 0° C., and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was washed with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-ethyl acetate) to give ethyl 3-(2-fluoro-4-{({6-isopropoxy-2′,6′-dimethyl-4′-[(1-oxidotetrahydro-2H-thiopyran-4-yl)oxy]biphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (0.42 g, yield 61%, 2 steps) as a pale-yellow oil. To a solution of the obtained ethyl 3-(2-fluoro-4-{({6-isopropoxy-2′,6′-dimethyl-4′-[(1-oxidotetrahydro-2H-thiopyran-4-yl)oxy]biphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (0.42 g, 0.54 mmol) in ethyl acetate (6 mL) was added m-chloroperbenzoic acid (70%, 0.15 g, 0.59 mmol) under stirring at 0° C., and the mixture was stirred at the same temperature for 1.5 hr. The reaction mixture was washed with 1 M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (0.40 g, yield 93%) as a colorless oil.