Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C:12]1([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](O)=[O:24])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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:23](=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1To a solution of 0.130 g of the above crude 5,6,7,8-tetrahydro-4H-furo[2,3-c]azepine hydrochloride, 0.18 g (0.96 mmol) of 6-phenylhexanoic acid and 0.44 ml (3.2 mmol) of triethylamine in 30 ml of dichloromethane, 0.15 ml (0.96 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 column chromatography (hexane/ethyl acetate=3/1 to 2/1) to yield the desired product.
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