[H-].[Na+].[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][NH2:16])[CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH3:6].Cl[CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27].O>CN(C=O)C>[CH2:3]([O:7][C:8]1[CH:9]=[C:10]([CH:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][NH:16][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH3:6]To a suspension of NaH (60%, 2.0 g, 51 mmol) in dry DMF (125 ml) cooled at 0° C., a solution of 2-(3-butoxyphenyl)-(tert-butoxycarbonyl)ethylamine (7.5 g, 25.5 mmol) in dry DMF (125 ml) was added dropwise. After 1 h at room temperature, 2-chloro-N,N-dimethylacetamide (5.2 ml, 51 mmol) was added and the mixture was stirred for 16 h at room temperature. H2O (10 ml) was added and the solvent was evaporated under reduced pressure. The residue was dissolved in H2O (150 ml) and extracted with CH2Cl2 (2×150 ml). The collected organic phases were dried over Na2SO4, filtered and evaporated. The crude was purified by flash chromatography (petroleum ether/EtOAc 4:6) affording the title compound (7.2 g, 75%) as light yellow oil.
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