[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].ClCCl.[F:10][C:11]1[CH:12]=[C:13]([C@H:18]2[NH:23][C@@H:22]([CH:24]([OH:26])[CH3:25])[CH2:21][O:20][CH2:19]2)[CH:14]=[CH:15][C:16]=1[F:17].N1C=CC=CC=1>O>[F:10][C:11]1[CH:12]=[C:13]([C@@H:18]2[CH2:19][O:20][CH2:21][C@@H:22]3[C@H:24]([CH3:25])[O:26][C:1](=[O:5])[C:2](=[O:3])[N:23]23)[CH:14]=[CH:15][C:16]=1[F:17]Under ice-cooling, oxalyl chloride (417 μL) was added dropwise into a dichloromethane (8 mL) solution of 1-[(3R,5R)-5-(3,4-difluorophenyl)morpholin-3-yl]ethanol (424 mg) and pyridine (2 mL). Stirring was continued for 30 minutes at the same temperature. Water was added to the reaction solution, and the organic layer was partitioned, and the resultant was dried with magnesium sulfate, and the solvent was removed under a vacuum. The residue was purified with silica gel column chromatography (heptane/ethyl acetate 9/1→1/4), and the title compound (353 mg) was obtained. The physical property values are as follows.
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