S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[C:12]([CH3:29])=[C:13]([CH:22]2[CH2:27][NH:26][C:25](=[O:28])[CH2:24][O:23]2)[C:14]([O:20][CH3:21])=[C:15]([CH:17](O)[CH3:18])[CH:16]=1>C(Cl)Cl>[Cl:10][C:11]1[C:12]([CH3:29])=[C:13]([CH:22]2[CH2:27][NH:26][C:25](=[O:28])[CH2:24][O:23]2)[C:14]([O:20][CH3:21])=[C:15]([CH:17]([Cl:3])[CH3:18])[CH:16]=1A mixture of thionyl chloride (15 μL, 0.21 mmol) and N,N-dimethylformamide (10.0 μL) was stirred at room temperature for 10 minutes. A solution of 6-[3-chloro-5-(1-hydroxyethyl)-6-methoxy-2-methylphenyl]morpholin-3-one (19.0 mg, 0.0634 mmol) (racemic mixture of two diastereomers from step 5) in methylene chloride (1.0 mL) was added and the mixture was stirred at room temperature overnight. The mixture was diluted with methylene chloride, washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and concentrated to give the desired compound as a racemic mixture of two diastereomers, 19 mg, 94%. LCMS calculated for C14H17ClNO3 (M-Cl)+: m/z=282.1; found: 282.1.
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