[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:6][CH:5]=1.Cl.[CH3:20][NH:21][O:22][CH3:23].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:23][O:22][N:21]([CH3:20])[C:14](=[O:16])[CH2:13][CH2:12][C:11]#[C:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:18])[F:17])=[CH:9][CH:8]=1
To a solution of 5-(4-trifluoromethoxy-phenyl)-pent-4-ynoic acid (1.0 g, 3.87 mmol; example 10 b]) in CH2Cl2 (50 ml) was added N,O-dimethylhydroxylamine hydrochloride (0.45 g, 4.65 mmol) and N-methylmorpholine (0.55 ml, 5 mmol). The mixture was cooled to 0° C. and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.97 g, 5 mmol) was added. The reaction solution was naturally warmed to ambient temperature, stirred over night and partitioned between aqueous 10% KHSO4/ether (three times). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl and dried (Na2SO4) to give 1.165 g (3.86 mmol, quant.) of the title compound as brown oil.
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