[Na].C(O)C.[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C@@H:15]([CH3:23])[C@H:16]([OH:22])[C:17](OCC)=[O:18])=[CH:9][NH:10]2.Br.[CH3:25][NH:26][C:27](NC)=[NH:28]>O>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH:15]([CH:16]1[O:22][C:27]([NH:26][CH3:25])=[N:28][C:17]1=[O:18])[CH3:23])=[CH:9][NH:10]2Sodium (100 mg) was dissolved into ethanol (5 ml). Ethyl (2S*,3R*)-3-(4-chloroindol-3-yl)-2-hydroxybutyrate (200 mg) and N,N′-dimethyl guanidine hydrogen bromide (143 mg) were added. The whole was refluxed for 16 hours. To the reaction mixture was added water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. Concentration of the solution gave a residue, which was subjected to silica gel chromatography. Elution with hexane-acetone (1:1) provided the titled compound (25 mg).
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