Propan-2-yl 2-aminoacetate → Isopropyl 2-((diphenylmethylene)amino)-5-oxo-4-(2,3,6-trifluorophenyl)hexanoate

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[NH2:1][CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=1[C:18](=[CH2:22])[C:19](=[O:21])[CH3:20].[C:23](O[Li])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[C:23]1([C:26](=[N:1][CH:2]([CH2:22][CH:18]([C:11]2[C:12]([F:17])=[CH:13][CH:14]=[C:15]([F:16])[C:10]=2[F:9])[C:19](=[O:21])[CH3:20])[C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:25]=[CH:22][CH:18]=[CH:19][CH:24]=1

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실험 절차

Diphenylidene isopropyl glycinate (2.0 g, 7.0 mmol) and 31 (1.4 g, 7.0 mmole) were dissolved in THF (10 ml). The solution was cooled to −10° C. tert-BuOLi (0.56 g, 7.0 mmole) was charged into the solution in several portions. The reaction was warmed up to room temperature slowly and stirred overnight. After quenched by addition of aqueous NH4Cl, the solvents were removed by distillation under vacuum. The residue was subjected to silica chromatography column eluted by hexane and EtOAc yielding 32 (3.0 g, 89%) as an oil, which was directly used in the next step.