[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:22]=[CH:21][C:10]([CH2:11][N:12]3[CH2:16][C@H:15]([C:17](O)=[O:18])[NH:14][C:13]3=[O:20])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH:25][N:26]1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C[Si](C)(C)CCON.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.O>[OH:25][NH:26][C:17]([C@H:15]1[CH2:16][N:12]([CH2:11][C:10]2[CH:21]=[CH:22][C:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=3)=[CH:8][CH:9]=2)[C:13](=[O:20])[NH:14]1)=[O:18]To a solution of (4R)-l -[4-(4-fluorophenoxy)benzyl]-2-oxo-imidazolidine-4-carboxylic acid (120 mg, 0.36 mmol) in methylene chloride (5 mL) were added sequentially 1-hydroxybenztria zole (73 mg, 0.54 mmol), diisopropylethylamine (0.13 mL, 0.75 mmol), O-(2-trimethylsilylethyl)hydroxylamine hydrochloride (92 mg, 0.54 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (104 mg, 0.54 mmol). The reaction mixture was stirred at room temperature for 16 hours and was then diluted with methylene chloride and water. The organic phase was washed successively with aqueous 1M HCI solution, water, aqueous saturated NaHCO3 solution and brine. After drying over MgSO4, the solution was concentrated to an oil. The title compound, an oil (85 mg, 53%), was isolated by chromatography on silica gel eluting with ethyl acetate.
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