Reaction SMILES: [CH2:1]([N:3](CC)CC)[CH3:2].CS(Cl)(=O)=O.[Si](O[CH2:21][CH2:22][CH:23]([F:42])[CH:24]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[O:34])=[CH:28][C:27]=1[F:41])O)(C(C)(C)C)(C)C.C(=O)(O)[O-:44].[Na+]>O.C(Cl)(Cl)Cl>[C:1]([N:3]1[CH2:21][CH2:22][CH:23]([F:42])[CH:24]1[C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[O:34])=[CH:28][C:27]=1[F:41])(=[O:44])[CH3:2]
Reactant: O=C([O-])O
Reactant: CCN(CC)CC
Reactant: CC(C)(C)[Si](C)(C)OCCC(F)C(O)c1ccc(NC(=O)c2ccccn2)cc1F
Agent: CS(=O)(=O)Cl
Agent: [Na+]
Solvent: O
Solvent: ClC(Cl)Cl
Product: CC(=O)N1CCC(F)C1c1ccc(NC(=O)c2ccccn2)cc1F
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
46 mg of triethylamine and 39 mg of methanesulfonyl chloride were added to a chloroform (5 ml) solution of 100 mg of N-(4-(4-((t-butyl(dimethyl)silyl)oxy)-2-fluoro-1-hydroxybutyl)-3-fluorophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 22 mg of sodium azide was added to a dimethylformamide (4 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled, water was added to it, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 0.3 ml of tetrabutylammonium fluoride (1.0 M tetrahydrofuran solution) was added to a tetrahydrofuran (4 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 1 hour. Water was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 46 mg of triethylamine and 39 mg of methanesulfonyl chloride were added in order to a chloroform (5 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 10 mg of copper sulfate pentahydrate and 50 mg of sodium borohydride were added in order to a methanol (4 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 1 hour. The reaction liquid was cooled, aqueous saturated sodium bicarbonate was added to it, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 46 mg of triethylamine, 35 mg of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine were added in order to a chloroform (4 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 30 minutes. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (chloroform/methanol=30/1) to obtain a diastereomer A and a diastereomer B of the entitled compound each as a colorless oily substance.