[C:1]1([CH2:7][CH2:8][N:9]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=2)[C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:30][CH:31]([CH2:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[F:30][CH:31]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:29][CH2:28][C:25]2[CH:24]=[CH:23][C:22]([CH2:21][N:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:10]3[S:11][CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=3)=[CH:27][CH:26]=2)=[CH:40][CH:39]=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33]To a solution of [4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]phenyl]methanol (725 mg, 1.81 mmol), ethyl 2-fluoro-3-(4-hydroxyphenyl)propanoate (300 mg, 1.81 mmol) and tributylphosphine (550 mg, 2.72 mmol) in tetrahydrofuran (30 mL) was added 1,1′-(azodicarbonyl)-dipiperidine (685 mg, 2.72 mmol), and the mixture was stirred at room temperature for 16 hr. The insoluble materials were filtered off and the filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:97-40:60) to give the title compound (798 mg, yield 78%, 2 steps) as a colorless oil.
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