[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[C:17]([C:25]([NH:27][C:28]3[C:29]([CH3:39])=[C:30]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:31]([O:33][CH3:34])=[O:32])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:16]=[C:17]([C:25]([NH:27][C:28]3[C:29]([CH3:39])=[C:30]([CH:35]=[CH:36][C:37]=3[CH3:38])[C:31]([O:33][CH3:34])=[O:32])=[O:26])[C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:14]1To a solution of methyl 3-[[3-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoate (0.30 g, 0.54 mmol) in THF (8.0 ml) is added Bu4NF 1.0 M in THF (0.35 g, 1.60 mmol) at 0° C. The reaction mixture is gradually warmed to ambient temperature. After 14 hours, the reaction mixture is diluted with ice-water and extracted with ethyl acetate. The organic layers are combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. The residue is purified by flash chromatography (silica gel) with ethyl acetate in hexanes to afford the title compound as a white solid (0.10 g, 55%). Mass spectrum (m/z): 433.0 (M+1).
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