C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13]([CH2:14][CH:15]2[S:19][C:18](=[O:20])[NH:17][C:16]2=[O:21])=[CH:12][CH:11]=1)[CH3:8].Br[CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:23]=[CH:22][C:13]([CH2:14][CH:15]2[S:19][C:18](=[O:20])[N:17]([CH2:25][CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:16]2=[O:21])=[CH:12][CH:11]=1)[CH3:8]Potassium carbonate (1.40 g, 9.68 mmol) was added to a solution of compound 4 (303 mg, 1.21 mmol) in 4 mL of anhydrous DMF at 0° C. After stifling the reaction mixture for 20 min, a solution of tert-butyl (2-bromoethyl)carbamate (268 mg, 1.21 mmol) in anhydrous DMF (2 mL) was added and then the reaction mixture was stirred at room temperature for 3 h. The reaction was quenched by adding water and then extracted with ethyl acetate. The ethyl acetate layer was washed with 10% NH4Cl aqueous solution followed by water and dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (20% ethyl acetate in hexanes) to afford compound 5 in 53.1% (253 mg) as a colorless oil.
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