Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[O:2]1[C:6]2[CH2:7][N:8]([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1To a solution of 0.270 g (1.692 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.36 g (1.9 mmol) of 6-phenylhexanoic acid and 0.94 ml (6.8 mmol) of triethylamine in 30 ml of dichloromethane, 0.39 ml (2.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (hexane/ethyl acetate=6/1 to 3/1) to yield the desired product.
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