Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:17]>C(C(C)=O)C(C)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH2:15][NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[CH:19][CH:20]=1A solution of glycine methyl ester hydrochloride (5.00 g, 39.8 mmol) in 80 ml methyl isobutyl ketone is treated with 12.6 g of sodium carbonate and the mixture stirred overnight at RT. Next, a solution of 2-bromo-1-(4-chlorophenyl)ethanone (8.37 g, 35.8 mmol) in 40 ml methyl isobutyl ketone is added dropwise to this suspension. The mixture is stirred for 1 hr more at RT, then the solid is suction-filtered and washed with 55 ml methyl isobutyl ketone. The filtrate is acidified with 12 ml of 6 N hydrochloric acid, then treated with 6.4 ml isopropanol. The precipitated solid is filtered off at the pump, washed with a little methyl isobutyl ketone, then stirred in 240 ml of acetonitrile and again suction-filtered. 3.41 g (34% of theory) of the pure title compound are thus obtained.
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