[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8](O)[CH2:9][N:10]([CH2:17][CH2:18]O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:33]([NH2:36])[CH:34]=[CH2:35].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:17][CH2:18][N:36]2[CH2:33][CH:34]=[CH2:35])=[CH:4][CH:3]=1
To (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(phenyl)amino]-1-ethanol (1.68 g, 4.94 mmol) produced in Example 11, ethyl acetate (10 mL) and triethylamine (1.75 g, 3.5 equivalents) were added. The mixture was cooled to 5° C. Methanesulfonyl chloride (1.81 g, 3.2 equivalents) was added dropwise thereto, and then allylamine (1.69 g, 6.0 equivalents) was added dropwise thereto. The mixture was stirred at 5° C. for 1 hour and then at 25° C. for 2 hours. The reaction mixture was transferred in an autoclave, and stirred at 50° C. for 18 hours. The mixture was cooled to room temperature, and then 10 wt % aqueous solution of sodium carbonate (8.38 g) was added to the mixture. After the organic layer and aqueous layer were separated, the organic layer was washed twice with distilled water (10 mL). The obtained organic layer was concentrated to give 1.11 g of a concentrate as yellow oil (chemical purity: 30.2 area %). The concentrate was purified by column chromatography (gel: silica gel, solvent: ethyl acetate/hexane=1/9), and the obtained fractions were concentrated and dried under vacuum, to obtain 307 mg of the title compound as colorless oil (yield: 19%, chemical purity: 98.1 area %). The retention time in the chemical purity analysis method was 56.6 min.
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