[CH3:1][O:2][NH:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[H-].[Na+].Cl[CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>C1COCC1>[CH3:1][O:2][N:3]([CH2:14][CH2:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7]To a cooled (0° C.) solution of tert-butyl methoxycarbamate (2.35 g, 16.0 mmol) in THF (50 mL) was slowly added NaH (0.640 g, 16.0 mmol). After stirring at 0° C. for 5 minutes and then at room temperature for 30 minutes, the mixture was added dropwise to a solution of 3-chloro-1-phenylpropan-1-one (2.84 g, 16.8 mmol) in THF (25 mL). After stirring at room temperature for 30 minutes, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was chromatographed (10% ethyl acetate in hexanes) to provide the product (1.80 g, 40% yield) as a clear oil.
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