Reaction SMILES: [CH3:1][C:2]1([CH3:29])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17][S:18][C:19]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:20]=3)[C:11]=2[CH3:28])[CH2:4][O:3]1.O.C([C@@H]([C@H](C(OCC)=O)O)O)(OCC)=[O:32].[O-]O.C1(C(C)C)C=CC=CC=1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:29])[O:3][CH2:4][CH:5]([CH2:8][O:9][C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17][S:18]([C:19]3[NH:20][C:21]4[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=4[N:23]=3)=[O:32])[C:11]=2[CH3:28])[CH2:6][O:7]1
Reactant: Cc1cnc(CSc2nc3ccccc3[nH]2)c(C)c1OCC1COC(C)(C)OC1
Reactant: CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC
Agent: [Ti+4]
Agent: CC(C)[O-]
Agent: O=S([O-])([O-])=S
Solvent: O
Solvent: Cc1ccccc1
Solvent: CC(C)c1ccccc1
Product: Cc1cnc(CS(=O)c2nc3ccccc3[nH]2)c(C)c1OCC1COC(C)(C)OC1
Temperature: 60 °C
Reaction time: 0.1 h

Procedure:
2-(((4-(2,2-dimethyl-1,3-dioxan-5-yl)methoxy-3,5-dimethylpyridin-2-yl)methyl)thio)-1H-benzimidazole (580.3 g, content: 96.5%, amount: 560.0 g, 1.354 mol), toluene (3864 mL), and H2O (2.81 g, 0.156 mol) were sequentially added in a nitrogen atmosphere and the mixture was stirred while heating at 60° C. After 6 minutes, diethyl L-(+)-tartrate (122.9 g, 0.596 mol) was added with toluene (560 mL) to the resultant suspension, and the bottle of the reagent was washed down. After 30 minutes, dissolution was confirmed. After 8 minutes, titanium (IV) tetraisopropoxide (77.0 g, 0.271 mol) was added and the bottle of the reagent was washed down with toluene (56 mL). The resultant mixture was stirred while heating at the same temperature for about one hour. The mixture was cooled to 8° C. and N,N-diisopropylethylamine with toluene (280 mL) was added (56.01 g, 0.742 mol), and then, the bottle of the reagent was washed down. After 10 minutes, a toluene solution (840 mL) of cumene hydroperoxide (259.2 g, 1.422 mol) was added dropwise for 47 minutes and the mixture was stirred at 8° C. for about 18.5 hours. A 30% w/w aqueous sodium thiosulfate solution (2240 g) cooled was poured and the mixture was stirred for 12 minutes, and then the aqueous layer was discarded. To the organic layer, a 4% w/w aqueous sodium hydroxide solution (2240 g) was poured and the mixture was stirred, and allowed to stand. The aqueous layer was separated to obtain an aqueous solution of an optical isomer (short in retention time) of 2-(((4-(2,2-dimethyl-1,3-dioxan-5-yl)methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole extracted with the aqueous sodium hydroxide solution as a brown-yellow suspension. To toluene (7840 mL), the solution (2.98 kg) of an optical isomer (short in retention time) of 2-(((4-(2,2-dimethyl-1,3-dioxan-5-yl)methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole extracted with the aqueous sodium hydroxide solution was poured and the mixture was stirred. To the mixture, a 20% w/w aqueous acetic acid solution (400 mL), a 8% aqueous NaOH solution (50 mL), and a 20% w/w aqueous acetic acid solution (8 mL) were sequentially added while stirring and pH was adjusted to 8.64. The mixture was allowed to stand and separated, and the aqueous layer was discarded. The organic layer was washed with a 5% w/w aqueous saline solution (2240 g), separated to obtain a toluene extraction solution of an optical isomer (short in retention time) of 2-(((4-(2,2-dimethyl-1,3-dioxan-5-yl)methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole (7.31 kg) (the content thereof: 567.7 g, 1.322 mol) as a brown-yellow solution.