[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH2:18]([O:20][C:21]([C:23]1([CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])[CH3:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:18]([O:20][C:21]([C:23]1([CH2:29][CH:30]2[CH2:31][CH2:32]2)[CH2:24][CH2:25][N:26]([C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:13][CH:12]=2)=[O:16])[CH2:27][CH2:28]1)=[O:22])[CH3:19]A mixture of 0.31 g (1.4 mmol) 4′-fluoro-biphenyl-4-carboxylic acid, 0.426 g (1.71 mmol) 4-cyclopropylmethyl-piperidine-4-carboxylic acid ethyl ester, hydrochloride, 0.552 g (1.71 mmol) TBTU and 1.23 mL DIPEA in 25 mL DMF was stirred at room temperature over night. After evaporation to dryness the residue was purified by column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product containing fractions 0.51 g (87%) of the title compound as light yellow viscous oil. MS ISP (m/e): 410.3 [(M+H)+].
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